Synthesis of macrotetrolide α, a designed polynactin analog composed of bishomononactic acids

Kentaro Takai, Tadaatsu Hanadate, Masaki Abe, Yukie Ono, Teiko Yamada, Shigefumi Kuwahara, Hiromasa Kiyota

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

Macrotetrolide α (1), a designed polynactin analog composed of (+)- and (-)-bishomononactic acids, was synthesized. The monomeric acids were prepared using cis-selective iodoetherification and optical resolution of the corresponding O-acetylmandelates as the key steps. Esterification and macrolactonization of the monomers were performed by Corey-Mukaiyama-Gerlach method. Compound 1 showed no immunosuppressive activity contrary to other natural polynactin congeners.

Original languageEnglish
Pages (from-to)7066-7072
Number of pages7
JournalTetrahedron
Volume67
Issue number37
DOIs
Publication statusPublished - Sep 16 2011
Externally publishedYes

Keywords

  • Antibiotics
  • Bishomononactic acid
  • Macrotetrolides
  • Polynactin
  • Total synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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