Total Synthesis of Alcyonolide

Hitoshi Fumiyama, Arata Takahashi, Yuma Suzuki, Naoto Fujioka, Hirotake Matsumoto, Seijiro Hosokawa*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

The total synthesis of alcyonolide, an antitumor xenicn diterpenoid, has been achieved. The inverse electron demand hetero-Diels-Alder reaction using a dienophile possessing an electron-withdrawing group provided the endo adduct which included a condensed lactone and dihydropyran rings with the desired three stereogenic centers. After introduction of the side chain by the Negishi coupling, the lactone ring was opened to form a Weinreb amide. The sequential transformation including conversion of Weinreb amide to aldehyde, PMB to acetate, and allylation of the aldehyde gave a mixture of separable four diastereomers. The desired stereoisomer was submitted to the 2,2,6,6-tetramethylpiperidine 1-oxyl oxidation, which afforded the δ-lactone and the methyl ketone side chain. Finally, the olefin metathesis of the desired isomer gave racemic alcyonolide.

Original languageEnglish
Pages (from-to)15492-15498
Number of pages7
JournalJournal of Organic Chemistry
Volume87
Issue number22
DOIs
Publication statusPublished - 2022 Nov 18

ASJC Scopus subject areas

  • Organic Chemistry

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