Studies toward the total synthesis of irumamycin: stereoselective preparation of the C(15)-C(27) segment via two-directional chain synthesis

Tomoyasu Hirose, Toshiaki Sunazuka, Daisuke Yamamoto, Mutsumi Mouri, Yoshiaki Hagiwara, Takanori Matsumaru, Eisuke Kaji, Satoshi Omura

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6 Citations (Scopus)

Abstract

The basic structure of the C(15)-C(27) part of irumamycin (1) was synthesized. Stereoselective assembly of C16, 17, 22, and an extra C21 stereocenter was achieved by two-directional Brown's asymmetric allyl boration. Group selective PMP acetal formation and oxidative cleavage of vinyl group facilitated the differentiation of the ends of a two-directionally synthesized chain.

Original languageEnglish
Pages (from-to)413-416
Number of pages4
JournalTetrahedron Letters
Volume48
Issue number3
DOIs
Publication statusPublished - 2007 Jan 15
Externally publishedYes

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ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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