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

研究成果: Article査読

31 被引用数 (Scopus)

抄録

(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.

本文言語English
ページ(範囲)2261-2264
ページ数4
ジャーナルOrganic Letters
7
11
DOI
出版ステータスPublished - 2005 5月 26

ASJC Scopus subject areas

  • 生化学
  • 物理化学および理論化学
  • 有機化学

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