American Chemical Society
ja990404v_si_001.pdf (1.04 MB)

Enantiodivergent Total Syntheses of (+)- and (−)-Scopadulcic Acid A

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journal contribution
posted on 1999-05-20, 00:00 authored by Martin E. Fox, Chi Li, Joseph P. Marino, Larry E. Overman
The first enantioselective total synthesis of scopadulcic acid A is described. The key step is a cascade intramolecular Heck reaction of a methylenecycloheptene iodide, which generates the B, C, and D rings of the scopadulan ring system in 90% yield as a single stereoisomer. A distinctive feature of these syntheses is the use of stereoselective enolization to dictate which enantiomer of the natural product is produced.