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Total Syntheses of Scabrolide B, Ineleganolide, and Related Norcembranoids
Emma J Simmons1,2, David B Ryffel1,2, Diego A Lopez2
1Department of Chemistry, Rice University, Houston, Texas 77005, United States.
Abstract:
Concise total syntheses of several 5/7/6 norcembranoids, including ineleganolide, scabrolide B, sinuscalide C, and fragilolide A have been achieved through a fragment coupling/ring closure approach. The central seven-membered ring was forged through sequential Mukaiyama-Michael/aldol reactions using norcarvone and a decorated bicyclic lactone incorporating a latent electrophile. Subsequent manipulations installed the reactive enedione motif and delivered scabrolide B in 11 steps from a chiral pool-derived enone. Finally, ineleganolide, sinuscalide C, and fragilolide A were each accessed in one additional step.
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