Total synthesis and absolute configuration of koshikalide

Kazuki Kunifuda, Arihiro Iwasaki, Masashi Nagamoto, Kiyotake Suenaga

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

The first total synthesis of koshikalide, a 14-membered macrolide that contains three olefins, was achieved. The skipped diene in the cyclic system was efficiently constructed by very mild Stille coupling at low temperature. The absolute stereochemistry was established by comparison of the specific optical rotations of natural and synthesized koshikalide.

Original languageEnglish
Pages (from-to)3121-3123
Number of pages3
JournalTetrahedron Letters
Volume57
Issue number29
DOIs
Publication statusPublished - 2016 Jul 20

Fingerprint

Optical rotation
Optical Rotation
Stereochemistry
Macrolides
Alkenes
Temperature

Keywords

  • Koshikalide
  • Macrolide
  • Marine cyanobacteria
  • Marine natural products
  • Total synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Total synthesis and absolute configuration of koshikalide. / Kunifuda, Kazuki; Iwasaki, Arihiro; Nagamoto, Masashi; Suenaga, Kiyotake.

In: Tetrahedron Letters, Vol. 57, No. 29, 20.07.2016, p. 3121-3123.

Research output: Contribution to journalArticle

Kunifuda, Kazuki ; Iwasaki, Arihiro ; Nagamoto, Masashi ; Suenaga, Kiyotake. / Total synthesis and absolute configuration of koshikalide. In: Tetrahedron Letters. 2016 ; Vol. 57, No. 29. pp. 3121-3123.
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