Kinetically controlled one-pot formation of DEFGH-rings of type B physalins through domino-type transformations

Masaki Morita, Go Hirai, Megumi Ohkubo, Hiroyuki Koshino, Daisuke Hashizume, Keiji Maruoka, Mikiko Sodeoka

Research output: Contribution to journalArticlepeer-review

9 Citations (Scopus)

Abstract

The characteristic DEFGH-ring system of type B physalins has been synthesized by means of a one-pot procedure incorporating domino-type ring transformations. Unexpectedly, we found that introduction of an α-hydroxyester functionality at C17 in ring E allowed the key 7-endo oxy-Michael reaction to proceed. Originally this was thought to be an unfavored process. This afforded the desired caged ring system to be formed in a kinetically controlled manner. Consecutive treatment with AcOH at 100 °C furnished the DEFGH-ring system in one pot.

Original languageEnglish
Pages (from-to)3434-3437
Number of pages4
JournalOrganic Letters
Volume14
Issue number13
DOIs
Publication statusPublished - Jul 6 2012
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

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