Short Flow-Photochemistry Enabled Synthesis of the Cytotoxic Lactone (+)-Goniofufurone

Michael J Robertson-Ralph, Sean Ng, Kevin I Booker-Milburn

Research output: Contribution to journalArticle (Academic Journal)peer-review

17 Citations (Scopus)
362 Downloads (Pure)

Abstract

A photochemical approach to the cytotoxic lactone (+)-goniofufurone (1) is reported. Paterno−̀ Büchi [2 + 2] photo- cycloaddition from known enol ether 4, derived from the readily available sugar D-isosorbide, yielded oxetane 7. This slow, dilute reaction was scaled up by using flow photochemistry to yield >40 g of 7. Installation of the key lactone ring was achieved via a unique Wacker- style oxidation of an enol−ether bond. Acid-catalyzed aqueous ring opening provided 1 in five steps from 4 (11.5% overall).
Original languageEnglish
Pages (from-to)968-971
Number of pages4
JournalOrganic Letters
Volume18
Issue number5
Early online date18 Feb 2016
DOIs
Publication statusPublished - 4 Mar 2016

Structured keywords

  • BCS and TECS CDTs

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