DOI: 10.1002/ange.201302847. Biomimetic Dehydrogenative Diels–Alder Cycloadditions: Total Syntheses of Brosimones A and B

Biomimetic Dehydrogenative Diels–Alder Cycloadditions: Total Syntheses of Brosimones A and B

10.1002/ange.201302847

Crossref journal-article

Wiley

Angewandte Chemie (311)

Bibliography

Qi, C., Cong, H., Cahill, K. J., MÃ¼ller, P., Johnson, R. P., & Porco, J. A. (2013). Biomimetic Dehydrogenative DielsâAlder Cycloadditions: Total Syntheses of BrosimonesâA and B. Angewandte Chemie, 125(32), 8503â8506. Portico.

Authors 6

Chao Qi (first)
Huan Cong (additional)
Katharine J. Cahill (additional)
Peter Müller (additional)
Richard P. Johnson (additional)
John A. Porco (additional)

References 67 Referenced 16

For reviews see:
{'key': 'e_1_2_2_2_2', 'volume-title': 'Classics in Total Synthesis: Targets, Stratergies, Methods', 'author': 'Nicolaou K. C.', 'year': '1996'} / Classics in Total Synthesis: Targets, Stratergies, Methods by Nicolaou K. C. (1996)
{'key': 'e_1_2_2_3_2', 'volume-title': 'Biologically Active Natural Products: Pharmaceuticals', 'year': '2000'} / Biologically Active Natural Products: Pharmaceuticals (2000)
{'key': 'e_1_2_2_4_2', 'volume-title': 'Classics in Total Synthesis II: More Targets, Strategies, Methods', 'author': 'Nicolaou K. C.', 'year': '2003'} / Classics in Total Synthesis II: More Targets, Strategies, Methods by Nicolaou K. C. (2003)
10.1002/9780470742761
{'key': 'e_1_2_2_6_2', 'volume-title': 'Classics in Total Synthesis III', 'author': 'Nicolaou K. C.', 'year': '2011'} / Classics in Total Synthesis III by Nicolaou K. C. (2011)
For reviews see:
10.1002/ange.200200534
10.1002/anie.200200534
10.1002/ange.200200545
10.1002/anie.200200545
{'key': 'e_1_2_2_10_2', 'volume-title': 'Biomimetic Organic Synthesis, Vol.\u20051&2', 'year': '2011'} / Biomimetic Organic Synthesis, Vol. 1&2 (2011)
10.1002/cctc.200900323
For recent examples of dehydrogenative [4+2] cycloadditions see:
10.1039/b910198e
10.1021/ja1102037
10.1021/ol202283d
10.1021/ja2059704
10.1021/ja208162w
10.1021/ja3084708
10.1248/yakushi.121.535
10.1039/C39920001177
10.1021/ja803094u
10.1016/S0040-4039(01)90496-4
10.1021/ol9026705
10.5012/bkcs.2008.29.6.1199
10.1039/c2ob25115a
For [4+2] cycloadditions with AgNPs see:
10.1021/ja102482b
10.1016/j.tetlet.2011.02.023
10.1021/cs200495s
10.1021/ol300800r
{'key': 'e_1_2_2_32_2', 'first-page': '775', 'volume-title': 'Biomimetic Organic Synthesis, Vol.\u20052', 'author': 'Minami A.', 'year': '2011'} / Biomimetic Organic Synthesis, Vol. 2 by Minami A. (2011)
10.1016/S0040-4020(01)90109-7
10.3987/COM-89-4791
10.1039/c2np20034a
For complete experimental details see the Supporting Information.
For dehydrogenation of alkanes to alkenes using platinum see:
10.1021/ie0203680
10.1016/j.ijhydene.2007.12.037
10.1039/c0cc02865g
10.1021/ja302710v
10.1016/0022-328X(96)06116-5
10.1016/S0040-4039(00)96841-2
10.1016/S0040-4039(01)02137-2
CCDC 927682 (14) 927684 (18) 927685 (20) and 927683 (21) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre viawww.ccdc.cam.ac.uk/data_request/cif.
For dehydrogenation of alkenes to dienes using DDQ see:
10.1071/CH9921069
10.1021/jo981024f
10.1021/ol1003753
The structure of15was assigned by comparison to its hexamethyl ether derivative21 which was characterized by X‐ray crystal‐structure analysis.
DDQ adduct16was isolated in 44 % yield in the absence of AgNPs in which case cycloadduct15was not observed. For experimental details see the Supporting Information.
10.1002/ange.201002108
10.1002/anie.201002108
10.1039/c1ob06489d
For structural and conformational studies of [3 3]metacyclophane see:
10.1021/ja00311a047
10.1021/jo00050a031
10.1021/jo062220m
10.1021/cm970613j
10.1021/es9035557
For radical cation‐mediated stepwise cycloadditions see:
10.1021/ja983993y
10.1021/ja026924z
10.1021/jo8002562

Dates

Type	When
Created	12 years, 1 month ago (July 1, 2013, 11:19 a.m.)
Deposited	1 year, 10 months ago (Oct. 16, 2023, 7:11 p.m.)
Indexed	1 year, 10 months ago (Oct. 17, 2023, 6:58 p.m.)
Issued	12 years, 1 month ago (July 1, 2013)
Published	12 years, 1 month ago (July 1, 2013)
Published Online	12 years, 1 month ago (July 1, 2013)
Published Print	12 years ago (Aug. 5, 2013)

Funders 0

None

BibTeX

@article{Qi_2013, title={Biomimetic Dehydrogenative Diels–Alder Cycloadditions: Total Syntheses of Brosimones A and B}, volume={125}, ISSN={1521-3757}, url={http://dx.doi.org/10.1002/ange.201302847}, DOI={10.1002/ange.201302847}, number={32}, journal={Angewandte Chemie}, publisher={Wiley}, author={Qi, Chao and Cong, Huan and Cahill, Katharine J. and Müller, Peter and Johnson, Richard P. and Porco, John A.}, year={2013}, month=jul, pages={8503–8506} }

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