The first total synthesis of sporiolide A

Yuguo Du, Qi Chen, Robert J. Linhardt

Research output: Contribution to journalArticlepeer-review

26 Scopus citations

Abstract

The first total synthesis of the natural cytotoxic agent sporiolide A has been accomplished from D-glucal in 16 steps with 6.1% overall yield. Carbohydrates were applied as the chiral templates to manipulate the absolute configuration during the synthesis. Pyridinium chlorochromate (PCC)-promoted transformation of the cyclic enol-ether to lactone, followed by Yamaguchi esterification and intramolecular ring closure metathesis, greatly facilitates synthesis of the target compound.

Original languageEnglish
Pages (from-to)8446-8451
Number of pages6
JournalJournal of Organic Chemistry
Volume71
Issue number22
DOIs
StatePublished - 27 Oct 2006
Externally publishedYes

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