Synthesis of 3-Oxaterpenoids and Its Application in the Total Synthesis of (±)-Moluccanic Acid Methyl Ester

Cascades: An InBr3‐catalyzed intermolecular polyene cyclization initiated by a Prins reaction provides a concise approach to 3‐oxaterpenoid derivatives. The reaction is compatible with various aldehydes, ketones, and polyolefin–alcohol substrates. In addition, the total synthesis of (±)‐moluccanic a...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2012-10, Vol.51 (42), p.10619-10623
Main Authors: Li, Bin, Lai, Yin-Chang, Zhao, Yujun, Wong, Yiu-Hang, Shen, Zhi-Liang, Loh, Teck-Peng
Format: Article
Language:English
Subjects:
Aldehydes
Cascades
Compatibility
Cyclization
Derivatives
Esters
Indium - chemistry
indium bromide
Ketones
Molecular Structure
Naphthalenes - chemical synthesis
polyenes
Polyenes - chemistry
Prins reaction
Propionates - chemical synthesis
Stereoisomerism
Synthesis
Terpenes - chemical synthesis
Terpenes - chemistry
terpenoids
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Summary:Cascades: An InBr3‐catalyzed intermolecular polyene cyclization initiated by a Prins reaction provides a concise approach to 3‐oxaterpenoid derivatives. The reaction is compatible with various aldehydes, ketones, and polyolefin–alcohol substrates. In addition, the total synthesis of (±)‐moluccanic acid methyl ester was achieved in seven steps by using such a Prins–polyene cyclization as the key step.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201205981