Asymmetric total synthesis of (-)-merrilactone A: Use of a bulky protecting group as long-range stereocontrolling element

Masayuki Inoue; Takaaki Sato; Masahiro Hirama

doi:10.1002/anie.200601358

Asymmetric total synthesis of (-)-merrilactone A: Use of a bulky protecting group as long-range stereocontrolling element

Masayuki Inoue, Takaaki Sato, Masahiro Hirama

Research output: Contribution to journal › Article › peer-review

71 Citations (Scopus)

Abstract

(Chemical Equation Presented) Designer elegance: The transannular aldol reaction of a cyclooctene diketone is the key step in this total synthesis of the natural enantiomer of merrilactone A (see scheme). The configuration of the two stereocenters generated in the formation of the central bicyclo[3.3.0]octane framework of the natural product was established using a specially designed bulky protecting group.

Original language	English
Pages (from-to)	4843-4848
Number of pages	6
Journal	Angewandte Chemie - International Edition
Volume	45
Issue number	29
DOIs	https://doi.org/10.1002/anie.200601358
Publication status	Published - 2006 Jul 17
Externally published	Yes

Keywords

Aldol reaction
Asymmetric synthesis
Medium-ring compounds
Protecting groups
Terpenoids

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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10.1002/anie.200601358

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AU - Hirama, Masahiro

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AB - (Chemical Equation Presented) Designer elegance: The transannular aldol reaction of a cyclooctene diketone is the key step in this total synthesis of the natural enantiomer of merrilactone A (see scheme). The configuration of the two stereocenters generated in the formation of the central bicyclo[3.3.0]octane framework of the natural product was established using a specially designed bulky protecting group.

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KW - Asymmetric synthesis

KW - Medium-ring compounds

KW - Protecting groups

KW - Terpenoids

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Asymmetric total synthesis of (-)-merrilactone A: Use of a bulky protecting group as long-range stereocontrolling element

Abstract

Keywords

ASJC Scopus subject areas

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