11-Step Total Synthesis of Pallambins C and D

Luisruben P. Martinez, Shigenobu Umemiya, Sarah E. Wengryniuk, Phil S. Baran

Research output: Contribution to journalArticlepeer-review

25 Citations (Scopus)

Abstract

The structurally intriguing terpenes pallambins C and D have been assembled in only 11 steps from a cheap commodity chemical: furfuryl alcohol. This synthesis, which features a redox-economic approach free of protecting-group manipulations, assembles all four-ring systems via a sequential cyclization strategy. Of these four-ring constructing operations, two are classical (Robinson annulation and Mukaiyama aldol) and two are newly devised. During the course of this work a method for the difunctionalization of enol ethers was developed, and the scope of this transformation was explored.

Original languageEnglish
Pages (from-to)7536-7539
Number of pages4
JournalJournal of the American Chemical Society
Volume138
Issue number24
DOIs
Publication statusPublished - 2016 Jun 22
Externally publishedYes

ASJC Scopus subject areas

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

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