DOI: 10.1021/ja3089394. The Correct Structure of Aquatolide—Experimental Validation of a Theoretically-Predicted Structural Revision

The Correct Structure of Aquatolide—Experimental Validation of a Theoretically-Predicted Structural Revision

10.1021/ja3089394

Crossref journal-article

American Chemical Society (ACS)

Journal of the American Chemical Society (316)

Bibliography

Lodewyk, M. W., Soldi, C., Jones, P. B., Olmstead, M. M., Rita, J., Shaw, J. T., & Tantillo, D. J. (2012). The Correct Structure of AquatolideâExperimental Validation of a Theoretically-Predicted Structural Revision. Journal of the American Chemical Society, 134(45), 18550â18553.

Authors 7

Michael W. Lodewyk (first)
Cristian Soldi (additional)
Paul B. Jones (additional)
Marilyn M. Olmstead (additional)
Juan Rita (additional)
Jared T. Shaw (additional)
Dean J. Tantillo (additional)

References 33 Referenced 149

10.1016/S0040-4039(00)99142-1 / Tetrahedron Lett. by San Feliciano A. (1989)
10.1039/c2ob25717c / Org. Biomol. Chem. by Nouri D. H. (2012)
10.2174/138527206778742678 / Curr. Org. Chem. by Nouri D. H. (2006)
10.1021/ja003254t / J. Am. Chem. Soc. by Fedorov S. N. (2001)
10.1021/ja210837b / J. Am. Chem. Soc. by Quasdorf K. W. (2012)
10.1021/cr200106v / Chem. Rev. by Lodewyk M. W. (2012)
10.1021/np2000446 / J. Nat. Prod. by Lodewyk M. W. (2011)
dhttp://cheshirenmr.info(accessed Sept 14, 2012).
10.1021/jo200513q / J. Org. Chem. by Bally T. (2011)
10.1016/S0040-4039(00)95101-3 / Tetrahedron Lett. by San Feliciano A. (1985)
10.1016/S0040-4020(01)91377-8 / Tetrahedron by San Feliciano A. (1985)
10.1021/ja210986f / J. Am. Chem. Soc. by Trost B. M. (2012)
10.1021/ja00225a055 / J. Am. Chem. Soc. by Wender P. A. (1988)
10.1021/ja994053w / J. Am. Chem. Soc. by Paquette L. A. (2000)
10.1021/ja001946b / J. Am. Chem. Soc. by Limanto J. (2000)
10.1055/s-2000-6302 / Synthesis by Kraft M. E. (2000)
10.1021/jo010623a / J. Org. Chem. by Kraft M. E. (2001)
10.1039/c1cc11005e / Chem. Commun. by Liang Y. (2011)
10.1002/asia.201100805 / Chem.—Asian J. by Liang Y. (2012)
10.1021/ja00995a018 / J. Am. Chem. Soc. by Srinivasan R. (1967)
10.1021/ja00995a019 / J. Am. Chem. Soc. by Liu R. S. H. (1967)
10.1002/anie.198505661 / Angew. Chem., Int. Ed. Engl. by Gleiter R. (1985)
10.1021/cr60242a002 / Chem. Rev. by Dilling W. L. (1966)
aIt thus seems that [2 + 2] photocycloaddition of3cto form a bicyclo[2.1.1] structural unit is the likely biosynthetic route to aquatolide. The alternative photocycloaddition to form the originally proposed [2]ladderane structure apparently does not occur to any appreciable extent, at least inA. aquaticus. Interestingly, [2 + 2] photocycloaddition of myrcene, which could also lead to structures with bicyclo[2.1.1]hexane or [2]ladderane cores, has been shown to produce only the bicyclo[2.1.1]hexane product (see ref12b).
10.1016/S0040-4020(01)96422-1 / Tetrahedron by El Dahmy S. (1985)
10.1021/ja00878a025 / J. Am. Chem. Soc. by Meinwald J. (1962)
10.1002/bscb.19860950903 / Bull. Soc. Chim. Belg. by Bohlmann F. (1986)
{'key': 'ref17/cit17', 'first-page': '593', 'volume': '72', 'author': 'Schenk H.', 'year': '1999', 'journal-title': 'Croat. Chem. Acta'} / Croat. Chem. Acta by Schenk H. (1999)
10.1002/mrc.1188 / Magn. Reson. Chem. by Barfield M. (2003)
10.1016/S0040-4020(01)98361-9 / Tetrahedron by Wiberg K. B. (1965)
10.1021/ja00868a016 / J. Am. Chem. Soc. by Wiberg K. B. (1962)
10.1002/anie.200460864 / Angew. Chem., Int. Ed. by Nicolaou K. C. (2005)
10.1016/j.copbio.2010.09.003 / Curr. Opin. Biotechnol. by Molinski T. F. (2010)

Dates

Type	When
Created	12 years, 10 months ago (Oct. 29, 2012, 9:59 a.m.)
Deposited	2 years, 4 months ago (April 23, 2023, 7:39 p.m.)
Indexed	2 months ago (July 2, 2025, 1:14 p.m.)
Issued	12 years, 10 months ago (Nov. 5, 2012)
Published	12 years, 10 months ago (Nov. 5, 2012)
Published Online	12 years, 10 months ago (Nov. 5, 2012)
Published Print	12 years, 9 months ago (Nov. 14, 2012)

Funders 0

None

BibTeX

@article{Lodewyk_2012, title={The Correct Structure of Aquatolide—Experimental Validation of a Theoretically-Predicted Structural Revision}, volume={134}, ISSN={1520-5126}, url={http://dx.doi.org/10.1021/ja3089394}, DOI={10.1021/ja3089394}, number={45}, journal={Journal of the American Chemical Society}, publisher={American Chemical Society (ACS)}, author={Lodewyk, Michael W. and Soldi, Cristian and Jones, Paul B. and Olmstead, Marilyn M. and Rita, Juan and Shaw, Jared T. and Tantillo, Dean J.}, year={2012}, month=nov, pages={18550–18553} }

JSON

{
  "indexed": {
    "date-parts": [
      [
        2025,
        7,
        2
      ]
    ],
    "date-time": "2025-07-02T17:14:12Z",
    "timestamp": 1751476452869
  },
  "reference-count": 33,
  "publisher": "American Chemical Society (ACS)",
  "issue": "45",
  "content-domain": {
    "domain": [],
    "crossmark-restriction": false
  },
  "published-print": {
    "date-parts": [
      [
        2012,
        11,
        14
      ]
    ]
  },
  "DOI": "10.1021/ja3089394",
  "type": "journal-article",
  "created": {
    "date-parts": [
      [
        2012,
        10,
        29
      ]
    ],
    "date-time": "2012-10-29T13:59:39Z",
    "timestamp": 1351519179000
  },
  "page": "18550-18553",
  "source": "Crossref",
  "is-referenced-by-count": 149,
  "title": "The Correct Structure of Aquatolide\u2014Experimental Validation of a Theoretically-Predicted Structural Revision",
  "prefix": "10.1021",
  "volume": "134",
  "author": [
    {
      "given": "Michael W.",
      "family": "Lodewyk",
      "sequence": "first",
      "affiliation": [
        {
          "name": "Department of Chemistry, University of California, Davis, One Shields Avenue,\rDavis, California 95616, United States"
        }
      ]
    },
    {
      "given": "Cristian",
      "family": "Soldi",
      "sequence": "additional",
      "affiliation": [
        {
          "name": "Department of Chemistry, University of California, Davis, One Shields Avenue,\rDavis, California 95616, United States"
        }
      ]
    },
    {
      "given": "Paul B.",
      "family": "Jones",
      "sequence": "additional",
      "affiliation": [
        {
          "name": "Department of Chemistry, Wake Forest University, Winston-Salem, North Carolina\r27109, United States"
        }
      ]
    },
    {
      "given": "Marilyn M.",
      "family": "Olmstead",
      "sequence": "additional",
      "affiliation": [
        {
          "name": "Department of Chemistry, University of California, Davis, One Shields Avenue,\rDavis, California 95616, United States"
        }
      ]
    },
    {
      "given": "Juan",
      "family": "Rita",
      "sequence": "additional",
      "affiliation": [
        {
          "name": "Biology\rDepartment, Balearic Islands University, Palma de Mallorca, Spain"
        }
      ]
    },
    {
      "given": "Jared T.",
      "family": "Shaw",
      "sequence": "additional",
      "affiliation": [
        {
          "name": "Department of Chemistry, University of California, Davis, One Shields Avenue,\rDavis, California 95616, United States"
        }
      ]
    },
    {
      "given": "Dean J.",
      "family": "Tantillo",
      "sequence": "additional",
      "affiliation": [
        {
          "name": "Department of Chemistry, University of California, Davis, One Shields Avenue,\rDavis, California 95616, United States"
        }
      ]
    }
  ],
  "member": "316",
  "published-online": {
    "date-parts": [
      [
        2012,
        11,
        5
      ]
    ]
  },
  "reference": [
    {
      "key": "ref1/cit1",
      "doi-asserted-by": "crossref",
      "first-page": "2851",
      "DOI": "10.1016/S0040-4039(00)99142-1",
      "volume": "30",
      "author": "San Feliciano A.",
      "year": "1989",
      "journal-title": "Tetrahedron Lett."
    },
    {
      "key": "ref2/cit2a",
      "doi-asserted-by": "crossref",
      "first-page": "5514",
      "DOI": "10.1039/c2ob25717c",
      "volume": "10",
      "author": "Nouri D. H.",
      "year": "2012",
      "journal-title": "Org. Biomol. Chem."
    },
    {
      "key": "ref2/cit2b",
      "doi-asserted-by": "crossref",
      "first-page": "2055",
      "DOI": "10.2174/138527206778742678",
      "volume": "10",
      "author": "Nouri D. H.",
      "year": "2006",
      "journal-title": "Curr. Org. Chem."
    },
    {
      "key": "ref3/cit3",
      "doi-asserted-by": "crossref",
      "first-page": "504",
      "DOI": "10.1021/ja003254t",
      "volume": "123",
      "author": "Fedorov S. N.",
      "year": "2001",
      "journal-title": "J. Am. Chem. Soc."
    },
    {
      "key": "ref5/cit5a",
      "doi-asserted-by": "crossref",
      "first-page": "1396",
      "DOI": "10.1021/ja210837b",
      "volume": "134",
      "author": "Quasdorf K. W.",
      "year": "2012",
      "journal-title": "J. Am. Chem. Soc."
    },
    {
      "key": "ref5/cit5b",
      "doi-asserted-by": "crossref",
      "first-page": "1839",
      "DOI": "10.1021/cr200106v",
      "volume": "112",
      "author": "Lodewyk M. W.",
      "year": "2012",
      "journal-title": "Chem. Rev."
    },
    {
      "key": "ref5/cit5c",
      "doi-asserted-by": "crossref",
      "first-page": "1339",
      "DOI": "10.1021/np2000446",
      "volume": "74",
      "author": "Lodewyk M. W.",
      "year": "2011",
      "journal-title": "J. Nat. Prod."
    },
    {
      "key": "ref5/cit5d",
      "unstructured": "dhttp://cheshirenmr.info(accessed Sept 14, 2012)."
    },
    {
      "key": "ref6/cit6",
      "doi-asserted-by": "crossref",
      "first-page": "4818",
      "DOI": "10.1021/jo200513q",
      "volume": "76",
      "author": "Bally T.",
      "year": "2011",
      "journal-title": "J. Org. Chem."
    },
    {
      "key": "ref7/cit7",
      "doi-asserted-by": "crossref",
      "first-page": "2369",
      "DOI": "10.1016/S0040-4039(00)95101-3",
      "volume": "26",
      "author": "San Feliciano A.",
      "year": "1985",
      "journal-title": "Tetrahedron Lett."
    },
    {
      "key": "ref8/cit8",
      "doi-asserted-by": "crossref",
      "first-page": "5711",
      "DOI": "10.1016/S0040-4020(01)91377-8",
      "volume": "41",
      "author": "San Feliciano A.",
      "year": "1985",
      "journal-title": "Tetrahedron"
    },
    {
      "key": "ref9/cit9",
      "doi-asserted-by": "crossref",
      "first-page": "1474",
      "DOI": "10.1021/ja210986f",
      "volume": "134",
      "author": "Trost B. M.",
      "year": "2012",
      "journal-title": "J. Am. Chem. Soc."
    },
    {
      "key": "ref10/cit10a",
      "doi-asserted-by": "crossref",
      "first-page": "5904",
      "DOI": "10.1021/ja00225a055",
      "volume": "110",
      "author": "Wender P. A.",
      "year": "1988",
      "journal-title": "J. Am. Chem. Soc."
    },
    {
      "key": "ref10/cit10b",
      "doi-asserted-by": "crossref",
      "first-page": "2742",
      "DOI": "10.1021/ja994053w",
      "volume": "122",
      "author": "Paquette L. A.",
      "year": "2000",
      "journal-title": "J. Am. Chem. Soc."
    },
    {
      "key": "ref10/cit10c",
      "doi-asserted-by": "crossref",
      "first-page": "8071",
      "DOI": "10.1021/ja001946b",
      "volume": "122",
      "author": "Limanto J.",
      "year": "2000",
      "journal-title": "J. Am. Chem. Soc."
    },
    {
      "key": "ref10/cit10d",
      "doi-asserted-by": "crossref",
      "first-page": "1020",
      "DOI": "10.1055/s-2000-6302",
      "author": "Kraft M. E.",
      "year": "2000",
      "journal-title": "Synthesis"
    },
    {
      "key": "ref10/cit10e",
      "doi-asserted-by": "crossref",
      "first-page": "7443",
      "DOI": "10.1021/jo010623a",
      "volume": "66",
      "author": "Kraft M. E.",
      "year": "2001",
      "journal-title": "J. Org. Chem."
    },
    {
      "key": "ref10/cit10f",
      "doi-asserted-by": "crossref",
      "first-page": "6659",
      "DOI": "10.1039/c1cc11005e",
      "volume": "47",
      "author": "Liang Y.",
      "year": "2011",
      "journal-title": "Chem. Commun."
    },
    {
      "key": "ref10/cit10g",
      "doi-asserted-by": "crossref",
      "first-page": "593",
      "DOI": "10.1002/asia.201100805",
      "volume": "7",
      "author": "Liang Y.",
      "year": "2012",
      "journal-title": "Chem.\u2014Asian J."
    },
    {
      "key": "ref12/cit12a",
      "doi-asserted-by": "crossref",
      "first-page": "4932",
      "DOI": "10.1021/ja00995a018",
      "volume": "89",
      "author": "Srinivasan R.",
      "year": "1967",
      "journal-title": "J. Am. Chem. Soc."
    },
    {
      "key": "ref12/cit12b",
      "doi-asserted-by": "crossref",
      "first-page": "4936",
      "DOI": "10.1021/ja00995a019",
      "volume": "89",
      "author": "Liu R. S. H.",
      "year": "1967",
      "journal-title": "J. Am. Chem. Soc."
    },
    {
      "key": "ref12/cit12c",
      "doi-asserted-by": "crossref",
      "first-page": "566",
      "DOI": "10.1002/anie.198505661",
      "volume": "24",
      "author": "Gleiter R.",
      "year": "1985",
      "journal-title": "Angew. Chem., Int. Ed. Engl."
    },
    {
      "key": "ref12/cit12d",
      "doi-asserted-by": "crossref",
      "first-page": "373",
      "DOI": "10.1021/cr60242a002",
      "volume": "66",
      "author": "Dilling W. L.",
      "year": "1966",
      "journal-title": "Chem. Rev."
    },
    {
      "key": "ref15/cit15a",
      "unstructured": "aIt thus seems that [2 + 2] photocycloaddition of3cto form a bicyclo[2.1.1] structural unit is the likely biosynthetic route to aquatolide. The alternative photocycloaddition to form the originally proposed [2]ladderane structure apparently does not occur to any appreciable extent, at least inA. aquaticus. Interestingly, [2 + 2] photocycloaddition of myrcene, which could also lead to structures with bicyclo[2.1.1]hexane or [2]ladderane cores, has been shown to produce only the bicyclo[2.1.1]hexane product (see ref12b)."
    },
    {
      "key": "ref15/cit15b",
      "doi-asserted-by": "crossref",
      "first-page": "309",
      "DOI": "10.1016/S0040-4020(01)96422-1",
      "volume": "41",
      "author": "El Dahmy S.",
      "year": "1985",
      "journal-title": "Tetrahedron"
    },
    {
      "key": "ref15/cit15c",
      "doi-asserted-by": "crossref",
      "first-page": "3722",
      "DOI": "10.1021/ja00878a025",
      "volume": "84",
      "author": "Meinwald J.",
      "year": "1962",
      "journal-title": "J. Am. Chem. Soc."
    },
    {
      "key": "ref16/cit16",
      "doi-asserted-by": "crossref",
      "first-page": "707",
      "DOI": "10.1002/bscb.19860950903",
      "volume": "95",
      "author": "Bohlmann F.",
      "year": "1986",
      "journal-title": "Bull. Soc. Chim. Belg."
    },
    {
      "key": "ref17/cit17",
      "first-page": "593",
      "volume": "72",
      "author": "Schenk H.",
      "year": "1999",
      "journal-title": "Croat. Chem. Acta"
    },
    {
      "key": "ref18/cit18a",
      "doi-asserted-by": "crossref",
      "first-page": "344",
      "DOI": "10.1002/mrc.1188",
      "volume": "41",
      "author": "Barfield M.",
      "year": "2003",
      "journal-title": "Magn. Reson. Chem."
    },
    {
      "key": "ref18/cit18b",
      "doi-asserted-by": "crossref",
      "first-page": "2749",
      "DOI": "10.1016/S0040-4020(01)98361-9",
      "volume": "21",
      "author": "Wiberg K. B.",
      "year": "1965",
      "journal-title": "Tetrahedron"
    },
    {
      "key": "ref18/cit18c",
      "doi-asserted-by": "crossref",
      "first-page": "1594",
      "DOI": "10.1021/ja00868a016",
      "volume": "84",
      "author": "Wiberg K. B.",
      "year": "1962",
      "journal-title": "J. Am. Chem. Soc."
    },
    {
      "key": "ref21/cit21",
      "doi-asserted-by": "crossref",
      "first-page": "1012",
      "DOI": "10.1002/anie.200460864",
      "volume": "44",
      "author": "Nicolaou K. C.",
      "year": "2005",
      "journal-title": "Angew. Chem., Int. Ed."
    },
    {
      "key": "ref22/cit22",
      "doi-asserted-by": "crossref",
      "first-page": "819",
      "DOI": "10.1016/j.copbio.2010.09.003",
      "volume": "21",
      "author": "Molinski T. F.",
      "year": "2010",
      "journal-title": "Curr. Opin. Biotechnol."
    }
  ],
  "container-title": "Journal of the American Chemical Society",
  "original-title": [],
  "language": "en",
  "link": [
    {
      "URL": "https://pubs.acs.org/doi/pdf/10.1021/ja3089394",
      "content-type": "unspecified",
      "content-version": "vor",
      "intended-application": "similarity-checking"
    }
  ],
  "deposited": {
    "date-parts": [
      [
        2023,
        4,
        23
      ]
    ],
    "date-time": "2023-04-23T23:39:36Z",
    "timestamp": 1682293176000
  },
  "score": 1,
  "resource": {
    "primary": {
      "URL": "https://pubs.acs.org/doi/10.1021/ja3089394"
    }
  },
  "subtitle": [],
  "short-title": [],
  "issued": {
    "date-parts": [
      [
        2012,
        11,
        5
      ]
    ]
  },
  "references-count": 33,
  "journal-issue": {
    "issue": "45",
    "published-print": {
      "date-parts": [
        [
          2012,
          11,
          14
        ]
      ]
    }
  },
  "alternative-id": [
    "10.1021/ja3089394"
  ],
  "URL": "http://dx.doi.org/10.1021/ja3089394",
  "relation": {},
  "ISSN": [
    "0002-7863",
    "1520-5126"
  ],
  "subject": [],
  "container-title-short": "J. Am. Chem. Soc.",
  "published": {
    "date-parts": [
      [
        2012,
        11,
        5
      ]
    ]
  }
}