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Updated: Mar 25, 2026

Functionalized Spirocyclic Heterocycle Synthesis and Cytotoxicity Assay
Published on: February 9, 2021
Short Flow-Photochemistry Enabled Synthesis of the Cytotoxic Lactone (+)-Goniofufurone
Michael Ralph1, Sean Ng2, Kevin I Booker-Milburn1
1School of Chemistry, University of Bristol , Cantock's Close, Bristol, BS8 1TS, U.K.
Abstract:
A photochemical approach to the cytotoxic lactone (+)-goniofufurone (1) is reported. Paternò-Büchi [2 + 2] photocycloaddition 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).
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