Total synthesis of (+)-tubelactomicin A. 1. Stereoselective synthesis of the lower-half segment by an intramolecular Diels-Alder approach

Toru Motozaki, Kiyoto Sawamura, Akari Suzuki, Keigo Yoshida, Tatsuo Ueki, Aiko Ohara, Ryosuke Munakata, Ken Ichi Takao, Kin Ichi Tadano

Research output: Contribution to journalArticlepeer-review

29 Citations (Scopus)

Abstract

(Chemical Equation Presented) Starting from diethyl (R)-malate, synthesis of the lower-half segment of (+)-tubelactomicin A, a 16-membered macrolide antibiotic, has been achieved. The synthesis involved the highly endo- and π-facial selective intramolecular Diels-Alder reaction achieved using a trisubstituted methacrolein derivative tethering a 10-carbon dienyne unit at the β-carbon, which in turn was prepared from a known allylated malic acid derivative.

Original languageEnglish
Pages (from-to)2261-2264
Number of pages4
JournalOrganic Letters
Volume7
Issue number11
DOIs
Publication statusPublished - 2005 May 26

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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