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

63 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 languageEnglish
Pages (from-to)4843-4848
Number of pages6
JournalAngewandte Chemie - International Edition
Volume45
Issue number29
DOIs
Publication statusPublished - 2006 Jul 17
Externally publishedYes

Keywords

  • Aldol reaction
  • Asymmetric synthesis
  • Medium-ring compounds
  • Protecting groups
  • Terpenoids

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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