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

Research output: Contribution to journalArticle

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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Acetals
irumamycin
C 27

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Studies toward the total synthesis of irumamycin : stereoselective preparation of the C(15)-C(27) segment via two-directional chain synthesis. / Hirose, Tomoyasu; Sunazuka, Toshiaki; Yamamoto, Daisuke; Mouri, Mutsumi; Hagiwara, Yoshiaki; Matsumaru, Takanori; Kaji, Eisuke; Omura, Satoshi.

In: Tetrahedron Letters, Vol. 48, No. 3, 15.01.2007, p. 413-416.

Research output: Contribution to journalArticle

Hirose, Tomoyasu ; Sunazuka, Toshiaki ; Yamamoto, Daisuke ; Mouri, Mutsumi ; Hagiwara, Yoshiaki ; Matsumaru, Takanori ; Kaji, Eisuke ; Omura, Satoshi. / Studies toward the total synthesis of irumamycin : stereoselective preparation of the C(15)-C(27) segment via two-directional chain synthesis. In: Tetrahedron Letters. 2007 ; Vol. 48, No. 3. pp. 413-416.
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