Total Synthesis of (-)-Reidispongiolide A, an Actin-Targeting Macrolide Isolated from the Marine Sponge Reidispongia coerulea

Ian Paterson, Kate Ashton, Robert Britton, Giuseppe Cecere, Gaelle Chouraqui, Gordon John Florence, Henner Knust, Jonathan Stafford

Research output: Contribution to journalArticlepeer-review

35 Citations (Scopus)

Abstract

A stereocontrolled total synthesis of the microfilament-destabilizing cytotoxic macrolide (−)-reidispongiolide A, isolated from the New Caledonian marine sponge Reidispongia coerulea, is described. This synthesis utilizes a convergent aldol-based strategy to construct the 26-membered macrolactone, followed by the late-stage coupling of a derived aldehyde with an N-vinylformamide-containing ketone subunit to install the full side chain. Two alternative routes were examined for the introduction of the 2E,4E-dienoate region, and a complex Mukaiyama aldol coupling was used to connect the northern and southern hemispheres to install the C13 stereocenter. This constitutes the first chemical synthesis of any member of the reidispongiolide/sphinxolide family of marine macrolides and unequivocally establishes the relative and absolute configuration.
Original languageEnglish
Pages (from-to)367-387
Number of pages21
JournalChemistry-An Asian Journal
Volume3
Issue number2
Early online date7 Jan 2008
DOIs
Publication statusPublished - 1 Feb 2008

Fingerprint

Dive into the research topics of 'Total Synthesis of (-)-Reidispongiolide A, an Actin-Targeting Macrolide Isolated from the Marine Sponge Reidispongia coerulea'. Together they form a unique fingerprint.

Cite this