Total syntheses of (+/-)-montanin A and (+/-)-teuscorolide

The first total syntheses of (+/-)-montanin A and (+/-)-teuscorolide have been achieved from an advanced precursor previously developed via a Diels-Alder strategy; in the synthetic sequence, the synthesis of montanin A was first accomplished in 8 steps, from which teuscorolide was readily achieved i...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2008-01 (39), p.4720-4722
Main Authors: Chen, I-Chia, Wu, Yen-Ku, Liu, Hsing-Jang, Zhu, Jiang-Liang
Format: Article
Language:English
Subjects:
Cyclization
Furans - chemical synthesis
Furans - chemistry
Molecular Conformation
Pentanols - chemistry
Spiro Compounds - chemical synthesis
Spiro Compounds - chemistry
Stereoisomerism
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Summary:The first total syntheses of (+/-)-montanin A and (+/-)-teuscorolide have been achieved from an advanced precursor previously developed via a Diels-Alder strategy; in the synthetic sequence, the synthesis of montanin A was first accomplished in 8 steps, from which teuscorolide was readily achieved in 2 steps by using a novel furan oxidative cyclization-retro-cyclization process as a key operation.
ISSN:1359-7345
1364-548X
DOI:10.1039/b807218c