Efficient Total Syntheses of (−)-Colombiasin A and (−)-Elisapterosin B: Application of the Cr-Catalyzed Asymmetric Quinone Diels-Alder Reaction

A made‐to‐order asymmetric catalytic reaction was applied in the key quinone Diels–Alder step of the total syntheses of the title compounds (see scheme for the synthesis of colombiasin A). The reaction was highly regio‐ and diastereoselective.

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Bibliographic Details
Published in	Angewandte Chemie International Edition Vol. 44; no. 37; pp. 6046 - 6050
Main Authors	Boezio, Alessandro A., Jarvo, Elizabeth R., Lawrence, Brian M., Jacobsen, Eric N.
Format	Journal Article
Language	English
Published	Weinheim WILEY-VCH Verlag 19.09.2005 WILEY‐VCH Verlag Wiley
Subjects	asymmetric catalysis Benzoquinones - chemistry Bridged-Ring Compounds - chemical synthesis Chemistry Chemistry, Multidisciplinary Chromium - chemistry cycloaddition Diterpenes - chemical synthesis metathesis Models, Molecular natural products Physical Sciences quinones Science & Technology Stereoisomerism natural products cycloaddition metathesis PSEUDOPTEROGORGIA-ELISABETHAE STRATEGY TETRACYCLIC FRAMEWORK quinones asymmetric catalysis TERPENOIDS DITERPENE
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ISSN	1433-7851 1521-3773
DOI	10.1002/anie.200502178

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Summary:	A made‐to‐order asymmetric catalytic reaction was applied in the key quinone Diels–Alder step of the total syntheses of the title compounds (see scheme for the synthesis of colombiasin A). The reaction was highly regio‐ and diastereoselective.
Bibliography:	istex:289512F2E86F9D4D707F02EDF3320B57DB7D50E4 ArticleID:ANIE200502178 ark:/67375/WNG-9BZVDGBX-8 This work was supported by the NIH (GM-59316). We are grateful to Dr. R. Staples for carrying out the X-ray crystal structure analyses. This work was supported by the NIH (GM‐59316). We are grateful to Dr. R. Staples for carrying out the X‐ray crystal structure analyses. Medline NIH RePORTER ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	1433-7851 1521-3773
DOI:	10.1002/anie.200502178