Asymmetric Synthesis of the 1-epi Aglycon of the Cripowellins A and B

The unusual [5.3.2]bicyclic structure of the insecticidal Amaryllidaceae alkaloids cripowellins A and B has been synthesized for the first time by a sequence of Sharpless dihydroxylation, ring‐closing metathesis (RCM), and intramolecular Heck reaction (see scheme). The asymmetric synthesis of the 1‐...

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Published inAngewandte Chemie (International ed.) Vol. 44; no. 24; pp. 3766 - 3769
Main Authors Enders, Dieter, Lenzen, Achim, Raabe, Gerhard
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 13.06.2005
WILEY‐VCH Verlag
Wiley
Subjects
alkaloids
Alkylation
Amaryllidaceae Alkaloids - chemical synthesis
Amaryllidaceae Alkaloids - chemistry
asymmetric syntheses
Chemistry
Chemistry, Multidisciplinary
Cyclization
Heck reactions
insecticides
Molecular Structure
Physical Sciences
ring-closing metatheses
Science & Technology
Stereoisomerism
SYSTEM
ORGANIC-SYNTHESIS
alkaloids
ring-closing metatheses
DIHYDROXYLATION
ETHERS
RING-CLOSING METATHESIS
HETEROCYCLES
Heck reactions
asymmetric syntheses
CONSTRUCTION
OLEFIN-METATHESIS
insecticides
INTRAMOLECULAR HECK REACTION
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Summary:The unusual [5.3.2]bicyclic structure of the insecticidal Amaryllidaceae alkaloids cripowellins A and B has been synthesized for the first time by a sequence of Sharpless dihydroxylation, ring‐closing metathesis (RCM), and intramolecular Heck reaction (see scheme). The asymmetric synthesis of the 1‐epi aglycon proceeds with virtually complete diastereo‐ and enantioselectivity (≥98 % de, ≥98 % ee) in 13 steps and an overall yield of 5.6 %.
Bibliography:This work was supported by the Deutsche Forschungsgemeinschaft (SFB 380) and the Fonds der Chemischen Industrie. We thank Prof. Rosenkranz, Prof. Stetter, Dr. Lieb, and their co-workers, Bayer AG, for valuable discussions at the beginning of this project.
ArticleID:ANIE200500556
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This work was supported by the Deutsche Forschungsgemeinschaft (SFB 380) and the Fonds der Chemischen Industrie. We thank Prof. Rosenkranz, Prof. Stetter, Dr. Lieb, and their co‐workers, Bayer AG, for valuable discussions at the beginning of this project.
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SourceType-Scholarly Journals-1
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ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200500556