Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5226022 | Tetrahedron | 2009 | 6 Pages |
Abstract
A new strategy for enantioselective assembly of the trisubstituted tetrahydrofuran ring has been established for synthesis of the C1-C12 acid fragment of amphidinolide T series marine macrolides. The key steps involve the SmI2-mediated highly enantioselective reductive coupling of an aldehyde with the (1S,2R)-N-methylephedrine-derived crotonate to form the cis-3,4-disubstituted γ-butyrolactone and the subsequent BF3-mediated 1,3-anti-selective allylation of the five-membered-ring oxocarbenium ion with allyltrimethylsilane. The desired C1-C12 acid fragment was obtained in >25% overall yield via a 9-step sequence.
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Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Jialu Luo, Huoming Li, Jinlong Wu, Xinglong Xing, Wei-Min Dai,