Construction of Successive Stereogenic Centers of ent -Kauranoid through an Oxidative Dearomatization/1,2-Shift Cascade

Yuki Imamura, Hikaru Mizutani, Masahisa Nakada*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

The construction of the successive stereogenic centers, including an all-carbon quaternary stereogenic center, of ent-kauranoid through an oxidative dearomatization/1,2-shift cascade is described. The developed cascade reaction of a substrate bearing a trans-2-(p-methoxyphenyl) vinyl group as the migrating group afforded the desired product in 83% yield. The 1,2-shift in the cascade is strongly affected by a stereoelectronic effect. The X-ray crystal structure of a compound bearing four successive stereogenic centers in the fused-ring moiety of ent-kauranoid diterpene, which was prepared by the oxidative dearomatization/1,2-shift cascade and subsequent stereoselective transformations, is also reported.

Original languageEnglish
Pages (from-to)1556-1562
Number of pages7
JournalSynlett
Volume33
Issue number15
DOIs
Publication statusPublished - 2022 Aug 29

Keywords

  • 1,2-shift reaction
  • dearomatization
  • diterpenes
  • kauranoid
  • quaternary carbon

ASJC Scopus subject areas

  • Organic Chemistry

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