Bioinspired Total Synthesis of Delitschiapyrone A

Kazuki Kurasawa, Eunsang Kwon, Shigefumi Kuwahara, Masaru Enomoto

Research output: Contribution to journalArticlepeer-review

10 Citations (Scopus)


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
Issue number15
Publication statusPublished - 2018 Aug 3


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