Unified Total Synthesis of Pentacyclic Stemoamide-type Alkaloids

Yasuki Soda, Yasukazu Sugiyama, Makoto Yoritate, Hayato Tajima, Kana Shibuya, Chisato Ogihara, Takeshi Oishi, Takaaki Sato, Noritaka Chida

Research output: Contribution to journalArticlepeer-review

Abstract

The collective synthesis of pentacyclic stemoamide-type alkaloids is recognized as a daunting task despite high demand for a comprehensive biological profiling of these natural products. In this Letter, we report a unified synthesis of seven pentacyclic alkaloids and two unnatural derivatives. The keys to success are (1) the chemoselective assembly of four five-membered building blocks, (2) the direct oxidation of pyrrolidine natural products to pyrrole derivatives, and (3) the stereodivergent construction of totally E- or Z-substituted butenolides.

Original languageEnglish
Pages (from-to)7502-7507
Number of pages6
JournalOrganic letters
Volume22
Issue number19
DOIs
Publication statusPublished - Oct 2 2020

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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