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

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

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...

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Veröffentlicht in:Journal of the American Chemical Society 1999-06, Vol.121 (23), p.5467-5480
Hauptverfasser: Fox, Martin E, Li, Chi, Marino, Joseph P, Overman, Larry E
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container_title Journal of the American Chemical Society
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creator Fox, Martin E
Li, Chi
Marino, Joseph P
Overman, Larry E
description 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.
doi_str_mv 10.1021/ja990404v
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title Enantiodivergent Total Syntheses of (+)- and (−)-Scopadulcic Acid A
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