DOI: 10.1002/anie.200800554. Synthesis of (−)‐Octalactin A by a Strategic Vanadium‐Catalyzed Oxidative Kinetic Resolution

Synthesis of (−)‐Octalactin A by a Strategic Vanadium‐Catalyzed Oxidative Kinetic Resolution

10.1002/anie.200800554

Crossref journal-article

Wiley

Angewandte Chemie International Edition (311)

Bibliography

Radosevich, A. T., Chan, V. S., Shih, H., & Toste, F. D. (2008). Synthesis of (â)âOctalactinâA by a Strategic VanadiumâCatalyzed Oxidative Kinetic Resolution. Angewandte Chemie International Edition, 47(20), 3755â3758. Portico.

Authors 4

Alexander T. Radosevich (first)
Vincent S. Chan (additional)
Hui‐Wen Shih (additional)
F. Dean Toste (additional)

References 53 Referenced 56

For general discussions on kinetic resolution see:
10.1002/9780470147276.ch4
10.1002/1615-4169(20010129)343:1<5::AID-ADSC5>3.0.CO;2-I
10.2174/1385272802666220128233001 / Curr. Org. Chem. by Hoveyda A. H. (1998)
10.1016/S0040-4020(03)01022-6
10.1002/ange.200460842
10.1002/anie.200460842
10.1021/ja0433424
10.1002/ange.200503852
10.1002/anie.200503852
10.1073/pnas.0511021103
10.1021/jo0610412
10.1021/ja00012a048
{'key': 'e_1_2_2_13_2', 'first-page': '97', 'volume': '18', 'author': 'Perchellet J. P.', 'year': '1998', 'journal-title': 'Anticancer Res.'} / Anticancer Res. by Perchellet J. P. (1998)
10.1021/ja00091a082
10.1021/ja00097a060
10.1016/S0040-4039(01)02078-0
10.1021/ja038353w
10.1002/chem.200500417
10.1021/cr050045o
{'key': 'e_1_2_2_22_2', 'first-page': '883', 'volume': '151', 'author': 'Darzens G.', 'year': '1911', 'journal-title': 'C. R. Hebd. Seances Acad. Sci.'} / C. R. Hebd. Seances Acad. Sci. by Darzens G. (1911)
10.1016/B978-0-08-052349-1.00035-4 / Comprehensive Organic Synthesis, Vol. 2 by in T. Rosen (1991)
10.1021/ja00346a071
Optimum conditions for the oxidation of the intermediate alkylborane involve a peracid oxidation; use of more traditional oxidation protocols (H2O2 NaOH or NaBO3) resulted in the formation of an undesired γ lactone.
See theSupporting Informationfor details.
10.1021/ja00011a006
10.1021/ja00393a040
10.1055/s-1993-22605
10.1039/p29890000503
10.1021/ar00013a003
10.1021/cr00097a010
Luche conditions (NaBH4 CeCl3 MeOH −78 °C) gave good yield but with poor diastereoselectivity (ca. 1.7:1) in favor of the undesired anti‐Felkin–Anh product (7‐epi‐12).
10.1021/jo9814694
{'key': 'e_1_2_2_37_2', 'first-page': '38', 'volume': '1', 'author': 'Bachmann W. E.', 'year': '1942', 'journal-title': 'Org. React.'} / Org. React. by Bachmann W. E. (1942)
10.1016/B978-0-08-052349-1.00085-8
10.1002/1099-0690(200207)2002:14<2193::AID-EJOC2193>3.0.CO;2-D
10.1021/jo030367x
{'key': 'e_1_2_2_43_2', 'first-page': '166', 'author': 'Commeiras L.', 'year': '2006', 'journal-title': 'Synthesis'} / Synthesis by Commeiras L. (2006)
10.1021/ol015903r
10.1021/ja00188a095
10.1007/978-3-322-84062-2_15
10.1246/cl.1982.1641
10.1016/S0020-1693(99)00300-X
10.1021/jo026551k
The spectroscopic data for synthetic (−)‐octalactin A are in full agreement with those of the natural material. See theSupporting Informationfor complete procedural and analytical details for all compounds.

Dates

Type	When
Created	17 years, 4 months ago (April 10, 2008, 5:30 a.m.)
Deposited	1 year, 10 months ago (Oct. 16, 2023, 11:47 p.m.)
Indexed	9 months, 2 weeks ago (Nov. 19, 2024, 11:12 a.m.)
Issued	17 years, 4 months ago (April 28, 2008)
Published	17 years, 4 months ago (April 28, 2008)
Published Online	17 years, 4 months ago (April 28, 2008)
Published Print	17 years, 4 months ago (May 5, 2008)

Funders 0

None

BibTeX

@article{Radosevich_2008, title={Synthesis of (−)‐Octalactin A by a Strategic Vanadium‐Catalyzed Oxidative Kinetic Resolution}, volume={47}, ISSN={1521-3773}, url={http://dx.doi.org/10.1002/anie.200800554}, DOI={10.1002/anie.200800554}, number={20}, journal={Angewandte Chemie International Edition}, publisher={Wiley}, author={Radosevich, Alexander T. and Chan, Vincent S. and Shih, Hui‐Wen and Toste, F. Dean}, year={2008}, month=apr, pages={3755–3758} }

JSON

{
  "indexed": {
    "date-parts": [
      [
        2024,
        11,
        19
      ]
    ],
    "date-time": "2024-11-19T16:12:13Z",
    "timestamp": 1732032733457
  },
  "reference-count": 53,
  "publisher": "Wiley",
  "issue": "20",
  "license": [
    {
      "start": {
        "date-parts": [
          [
            2008,
            4,
            10
          ]
        ],
        "date-time": "2008-04-10T00:00:00Z",
        "timestamp": 1207785600000
      },
      "content-version": "vor",
      "delay-in-days": 0,
      "URL": "http://onlinelibrary.wiley.com/termsAndConditions#vor"
    }
  ],
  "content-domain": {
    "domain": [],
    "crossmark-restriction": false
  },
  "published-print": {
    "date-parts": [
      [
        2008,
        5,
        5
      ]
    ]
  },
  "DOI": "10.1002/anie.200800554",
  "type": "journal-article",
  "created": {
    "date-parts": [
      [
        2008,
        4,
        10
      ]
    ],
    "date-time": "2008-04-10T09:30:15Z",
    "timestamp": 1207819815000
  },
  "page": "3755-3758",
  "source": "Crossref",
  "is-referenced-by-count": 56,
  "title": "Synthesis of (\u2212)\u2010Octalactin\u2005A by a Strategic Vanadium\u2010Catalyzed Oxidative Kinetic Resolution",
  "prefix": "10.1002",
  "volume": "47",
  "author": [
    {
      "given": "Alexander\u2005T.",
      "family": "Radosevich",
      "sequence": "first",
      "affiliation": []
    },
    {
      "given": "Vincent\u2005S.",
      "family": "Chan",
      "sequence": "additional",
      "affiliation": []
    },
    {
      "given": "Hui\u2010Wen",
      "family": "Shih",
      "sequence": "additional",
      "affiliation": []
    },
    {
      "given": "F.\u2005Dean",
      "family": "Toste",
      "sequence": "additional",
      "affiliation": []
    }
  ],
  "member": "311",
  "published-online": {
    "date-parts": [
      [
        2008,
        4,
        28
      ]
    ]
  },
  "reference": [
    {
      "key": "e_1_2_2_1_2",
      "unstructured": "For general discussions on kinetic resolution see:"
    },
    {
      "key": "e_1_2_2_2_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/9780470147276.ch4"
    },
    {
      "key": "e_1_2_2_3_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/1615-4169(20010129)343:1<5::AID-ADSC5>3.0.CO;2-I"
    },
    {
      "key": "e_1_2_2_4_2",
      "doi-asserted-by": "crossref",
      "first-page": "489",
      "DOI": "10.2174/1385272802666220128233001",
      "volume": "2",
      "author": "Hoveyda A. H.",
      "year": "1998",
      "journal-title": "Curr. Org. Chem."
    },
    {
      "key": "e_1_2_2_5_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/S0040-4020(03)01022-6"
    },
    {
      "key": "e_1_2_2_6_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/ange.200460842"
    },
    {
      "key": "e_1_2_2_6_3",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/anie.200460842"
    },
    {
      "key": "e_1_2_2_7_2",
      "unstructured": "\u00a0"
    },
    {
      "key": "e_1_2_2_8_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja0433424"
    },
    {
      "key": "e_1_2_2_9_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/ange.200503852"
    },
    {
      "key": "e_1_2_2_9_3",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/anie.200503852"
    },
    {
      "key": "e_1_2_2_10_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1073/pnas.0511021103"
    },
    {
      "key": "e_1_2_2_11_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/jo0610412"
    },
    {
      "key": "e_1_2_2_12_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja00012a048"
    },
    {
      "key": "e_1_2_2_13_2",
      "first-page": "97",
      "volume": "18",
      "author": "Perchellet J. P.",
      "year": "1998",
      "journal-title": "Anticancer Res."
    },
    {
      "key": "e_1_2_2_14_2",
      "unstructured": "\u00a0"
    },
    {
      "key": "e_1_2_2_15_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja00091a082"
    },
    {
      "key": "e_1_2_2_16_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja00097a060"
    },
    {
      "key": "e_1_2_2_17_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/S0040-4039(01)02078-0"
    },
    {
      "key": "e_1_2_2_18_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja038353w"
    },
    {
      "key": "e_1_2_2_19_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/chem.200500417"
    },
    {
      "key": "e_1_2_2_20_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/cr050045o"
    },
    {
      "key": "e_1_2_2_21_2",
      "unstructured": "\u00a0"
    },
    {
      "key": "e_1_2_2_22_2",
      "first-page": "883",
      "volume": "151",
      "author": "Darzens G.",
      "year": "1911",
      "journal-title": "C. R. Hebd. Seances Acad. Sci."
    },
    {
      "key": "e_1_2_2_23_2",
      "doi-asserted-by": "crossref",
      "first-page": "409",
      "DOI": "10.1016/B978-0-08-052349-1.00035-4",
      "author": "in T. Rosen",
      "year": "1991",
      "journal-title": "Comprehensive Organic Synthesis, Vol.\u20052"
    },
    {
      "key": "e_1_2_2_24_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja00346a071"
    },
    {
      "key": "e_1_2_2_25_2",
      "unstructured": "Optimum conditions for the oxidation of the intermediate alkylborane involve a peracid oxidation; use of more traditional oxidation protocols (H2O2 NaOH or NaBO3) resulted in the formation of an undesired \u03b3\u2005lactone."
    },
    {
      "key": "e_1_2_2_26_2",
      "unstructured": "See theSupporting Informationfor details."
    },
    {
      "key": "e_1_2_2_27_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja00011a006"
    },
    {
      "key": "e_1_2_2_28_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja00393a040"
    },
    {
      "key": "e_1_2_2_29_2",
      "unstructured": "\u00a0"
    },
    {
      "key": "e_1_2_2_30_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1055/s-1993-22605"
    },
    {
      "key": "e_1_2_2_31_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1039/p29890000503"
    },
    {
      "key": "e_1_2_2_32_2",
      "unstructured": "\u00a0"
    },
    {
      "key": "e_1_2_2_33_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ar00013a003"
    },
    {
      "key": "e_1_2_2_34_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/cr00097a010"
    },
    {
      "key": "e_1_2_2_35_2",
      "unstructured": "Luche conditions (NaBH4 CeCl3 MeOH \u221278\u2009\u00b0C) gave good yield but with poor diastereoselectivity (ca.\u20051.7:1) in favor of the undesired anti\u2010Felkin\u2013Anh product (7\u2010epi\u201012)."
    },
    {
      "key": "e_1_2_2_36_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/jo9814694"
    },
    {
      "key": "e_1_2_2_37_2",
      "first-page": "38",
      "volume": "1",
      "author": "Bachmann W. E.",
      "year": "1942",
      "journal-title": "Org. React."
    },
    {
      "key": "e_1_2_2_38_2",
      "unstructured": "\u00a0"
    },
    {
      "key": "e_1_2_2_39_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/B978-0-08-052349-1.00085-8"
    },
    {
      "key": "e_1_2_2_40_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/1099-0690(200207)2002:14<2193::AID-EJOC2193>3.0.CO;2-D"
    },
    {
      "key": "e_1_2_2_41_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/jo030367x"
    },
    {
      "key": "e_1_2_2_42_2",
      "unstructured": "\u00a0"
    },
    {
      "key": "e_1_2_2_43_2",
      "first-page": "166",
      "author": "Commeiras L.",
      "year": "2006",
      "journal-title": "Synthesis"
    },
    {
      "key": "e_1_2_2_44_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ol015903r"
    },
    {
      "key": "e_1_2_2_45_2",
      "unstructured": "\u00a0"
    },
    {
      "key": "e_1_2_2_46_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja00188a095"
    },
    {
      "key": "e_1_2_2_47_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1007/978-3-322-84062-2_15"
    },
    {
      "key": "e_1_2_2_48_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1246/cl.1982.1641"
    },
    {
      "key": "e_1_2_2_49_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/S0020-1693(99)00300-X"
    },
    {
      "key": "e_1_2_2_50_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/jo026551k"
    },
    {
      "key": "e_1_2_2_51_2",
      "unstructured": "The spectroscopic data for synthetic (\u2212)\u2010octalactin\u2005A are in full agreement with those of the natural material. See theSupporting Informationfor complete procedural and analytical details for all compounds."
    }
  ],
  "container-title": "Angewandte Chemie International Edition",
  "original-title": [],
  "language": "en",
  "link": [
    {
      "URL": "https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fanie.200800554",
      "content-type": "unspecified",
      "content-version": "vor",
      "intended-application": "text-mining"
    },
    {
      "URL": "https://onlinelibrary.wiley.com/doi/pdf/10.1002/anie.200800554",
      "content-type": "unspecified",
      "content-version": "vor",
      "intended-application": "similarity-checking"
    }
  ],
  "deposited": {
    "date-parts": [
      [
        2023,
        10,
        17
      ]
    ],
    "date-time": "2023-10-17T03:47:06Z",
    "timestamp": 1697514426000
  },
  "score": 1,
  "resource": {
    "primary": {
      "URL": "https://onlinelibrary.wiley.com/doi/10.1002/anie.200800554"
    }
  },
  "subtitle": [],
  "short-title": [],
  "issued": {
    "date-parts": [
      [
        2008,
        4,
        28
      ]
    ]
  },
  "references-count": 53,
  "journal-issue": {
    "issue": "20",
    "published-print": {
      "date-parts": [
        [
          2008,
          5,
          5
        ]
      ]
    }
  },
  "alternative-id": [
    "10.1002/anie.200800554"
  ],
  "URL": "http://dx.doi.org/10.1002/anie.200800554",
  "relation": {},
  "ISSN": [
    "1433-7851",
    "1521-3773"
  ],
  "subject": [],
  "container-title-short": "Angew Chem Int Ed",
  "published": {
    "date-parts": [
      [
        2008,
        4,
        28
      ]
    ]
  }
}