Synthetic Studies toward Sarain A. Formation of the Western Macrocyclic Ring

Starting with the tricyclic core 2b, annulation to form the 13-membered western ring of sarain A has been achieved to afford the macrocycle 30a by initial construction of the sterically congested quaternary center at C-3, followed by elaboration of the C-3 side-chain and ring-closing olefin metathes...

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Bibliographic Details
Published in:Journal of organic chemistry 2003-03, Vol.68 (6), p.2205-2208
Main Authors: Sung, Moo Je, Lee, Hyoung Ik, Lee, Hee Bong, Cha, Jin Kun
Format: Article
Language:English
Subjects:
Alkaloids - chemical synthesis
Animals
Bridged-Ring Compounds - chemical synthesis
Catalysis
Chemistry
Cyclization
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Indicators and Reagents
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Organic chemistry
Polycyclic Aromatic Hydrocarbons - chemical synthesis
Porifera - chemistry
Preparations and properties
Structure-Activity Relationship
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Summary:Starting with the tricyclic core 2b, annulation to form the 13-membered western ring of sarain A has been achieved to afford the macrocycle 30a by initial construction of the sterically congested quaternary center at C-3, followed by elaboration of the C-3 side-chain and ring-closing olefin metathesis. Also included is a parallel conversion of tricycle 2c to macrocycle 30b containing a functionalized side-chain at N-1 suitable for attachment of the eastern macrocyclic ring.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo026914g