Bioinspired Total Synthesis of Delitschiapyrone A

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3 Citations (Scopus)

Abstract

A bioinspired seven-step total synthesis of delitschiapyrone A was accomplished in 32% overall yield from commercially available 4-bromo-3,5-dimethoxybenzoic acid. The key step of the synthesis is an exclusively regioselective and diastereoselective reaction cascade consisting of the Diels-Alder reaction, α-ketol rearrangement, and cyclic hemiacetalization, achieved by simply stirring a heterogeneous mixture of two Diels-Alder substrates (putative biosynthetic intermediates) and water at 35 °C, directly furnishing the pentacyclic natural product in 75% yield. ©

Original languageEnglish
Pages (from-to)4645-4648
Number of pages4
JournalOrganic letters
Volume20
Issue number15
DOIs
Publication statusPublished - 2018 Aug 3

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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