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

4 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

Fingerprint

Esterification
Immunosuppressive Agents
Monomers
Acids
bishomononactic acid

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Synthesis of macrotetrolide α, a designed polynactin analog composed of bishomononactic acids. / Takai, Kentaro; Hanadate, Tadaatsu; Abe, Masaki; Ono, Yukie; Yamada, Teiko; Kuwahara, Shigefumi; Kiyota, Hiromasa.

In: Tetrahedron, Vol. 67, No. 37, 16.09.2011, p. 7066-7072.

Research output: Contribution to journalArticle

Takai, K, Hanadate, T, Abe, M, Ono, Y, Yamada, T, Kuwahara, S & Kiyota, H 2011, 'Synthesis of macrotetrolide α, a designed polynactin analog composed of bishomononactic acids', Tetrahedron, vol. 67, no. 37, pp. 7066-7072. https://doi.org/10.1016/j.tet.2011.07.012
Takai, Kentaro ; Hanadate, Tadaatsu ; Abe, Masaki ; Ono, Yukie ; Yamada, Teiko ; Kuwahara, Shigefumi ; Kiyota, Hiromasa. / Synthesis of macrotetrolide α, a designed polynactin analog composed of bishomononactic acids. In: Tetrahedron. 2011 ; Vol. 67, No. 37. pp. 7066-7072.
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