Synthesis of Pinguisane-Type Sesquiterpenoids Acutifolone A, Pinguisenol, and Bisacutifolones by a Diels-Alder Dimerization Reaction

The total synthesis of pinguisane‐type sesquiterpenoids, acutifolone A (1) and pinguisenol (2), has been achieved by using the Mukaiyama aldol reaction as the key step. The intermolecular Diels–Alder reaction of these monomeric natural products successfully led to stereoselective dimerization, leadi...

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Bibliographic Details
Published in:European Journal of Organic Chemistry 2007-11, Vol.2007 (31), p.5190-5197
Main Authors: Shiina, Junichi, Oikawa, Masataka, Nakamura, Kensuke, Obata, Rika, Nishiyama, Shigeru
Format: Article
Language:English
Subjects:
Autoxidation
Biomimetic synthesis
Liverwort
Terpenoids
Total synthesis
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Summary:The total synthesis of pinguisane‐type sesquiterpenoids, acutifolone A (1) and pinguisenol (2), has been achieved by using the Mukaiyama aldol reaction as the key step. The intermolecular Diels–Alder reaction of these monomeric natural products successfully led to stereoselective dimerization, leading to bisacutifolones A (3) and B (4). Theoretical calculations revealed that the dimerization reaction proceeded through the most stable transition state. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200700522