Stereocontrolled Construction of ABCD Tetracyclic Ring System with Vicinal All-Carbon Quaternary Stereogenic Centers of Calyciphylline A Type Alkaloids

Yusuke Sasano, Junpei Koyama, Kaori Yoshikawa, Naoki Kanoh, Eunsang Kwon, Yoshiharu Iwabuchi

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

A unique approach to the synthesis of an ABCD tetracyclic core bearing the vicinal all-carbon quaternary stereogenic centers of the calyciphylline A type alkaloids is reported. The synthesis features two C-C bond formations at a sterically congested position: one is an intramolecular pinacol coupling to construct the central A ring; the other is a semipinacol rearrangement to construct a quaternary stereogenic center adjacent to another quaternary center.

Original languageEnglish
Pages (from-to)3053-3056
Number of pages4
JournalOrganic letters
Volume20
Issue number10
DOIs
Publication statusPublished - 2018 May 18

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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