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Org. Biomol. Chem., 2006, 4, 323 - 330, DOI: 10.1039/b513774h
The first total synthesis of natural grenadamide
Thomas D. Avery, Julie A. Culbert and Dennis K. Taylor
A concise, high yielding route to the naturally occurring enantiomer of grenadamide utilizing a 3,6-disubstituted 1,2-dioxine starting material is presented. The route allows for ease in synthesizing grenadamide derivatives varying at cyclopropyl carbons 2 and 3, with access to both enantiomers. Evidence for phosphorus-assisted deprotonation of 1,2-dioxines is also discussed.
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