Unified Total Synthesis of Madangamines A, C, and E

Takahiro Suto, Yuta Yanagita, Yoshiyuki Nagashima, Shinsaku Takikawa, Yasuhiro Kurosu, Naoya Matsuo, Takaaki Satou, Noritaka Chida

Research output: Contribution to journalArticle

26 Citations (Scopus)

Abstract

A stereodivergent strategy for the synthesis of skipped dienes is developed. The method consists of hydroboration of allenes and Migita-Kosugi-Stille coupling, which allows for access to all four possible stereoisomers of the skipped dienes. The hydroboration is especially useful for providing both E-allylic and Z-allylic alcohols from the same allene by simply changing the organoborane reagent. The strategy was successfully applied to a unified total synthesis of the madangamine alkaloids via a common ABCE-tetracyclic intermediate with a (Z,Z)-skipped diene. The late-stage variation of the D-ring enabled the supply of synthetic madangamines A, C, and E for the first time.

Original languageEnglish
Pages (from-to)2952-2955
Number of pages4
JournalJournal of the American Chemical Society
Volume139
Issue number8
DOIs
Publication statusPublished - 2017 Mar 1

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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    Suto, T., Yanagita, Y., Nagashima, Y., Takikawa, S., Kurosu, Y., Matsuo, N., Satou, T., & Chida, N. (2017). Unified Total Synthesis of Madangamines A, C, and E. Journal of the American Chemical Society, 139(8), 2952-2955. https://doi.org/10.1021/jacs.7b00807