Total Synthesis and Determination of the Absolute Configuration of (+)-Intricatetraol

A victory for synthesis: The total synthesis of the marine triterpene polyether (+)‐intricatetraol (1) has revealed its absolute configuration, which could not be determined even by spectroscopic methods. The approach features the enantioselective construction of the unique vicinal bromochloro funct...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2007-01, Vol.46 (7), p.1132-1135
Main Authors: Morimoto, Yoshiki, Okita, Tatsuya, Takaishi, Mamoru, Tanaka, Takeshi
Format: Article
Language:English
Subjects:
asymmetric synthesis
configuration determination
halogen compounds
Heterocyclic Compounds, 4 or More Rings - chemical synthesis
Heterocyclic Compounds, 4 or More Rings - chemistry
Molecular Conformation
Molecular Structure
polyethers
Rhodophyta - chemistry
Squalene - analogs & derivatives
Squalene - chemical synthesis
Squalene - chemistry
Stereoisomerism
Terpenes - chemistry
Terpenes - isolation & purification
terpenoids
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Summary:A victory for synthesis: The total synthesis of the marine triterpene polyether (+)‐intricatetraol (1) has revealed its absolute configuration, which could not be determined even by spectroscopic methods. The approach features the enantioselective construction of the unique vicinal bromochloro functionality and an efficient olefin‐metathesis strategy that takes the C2 symmetry of the target into consideration.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200603806