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Catalytic Asymmetric Formal Total Synthesis of (-)-Triptophenolide and (+)-Triptolide

Wen-Dan Xu, Liang-Qun Li, Ming-Ming Li, Hui-Chun Geng, Hong-Bo Qin

Nat Prod Bioprospect. 2016 Jun;6(3):183-6.

PMID: 27095015

Abstract:

Catalytic asymmetric formal synthesis of (-)-Triptophenolide and (+)-Triptolide have been achieved. Key reaction involves Palladium catalyzed asymmetric conjugate addition of aryl boronic acid to 3-methyl cyclohexe-1-none to form quaternary carbon. Claisen rearrangement and subsequent aldol reaction furnished trans-decaline key intermediate, which assured a formal total synthesis of (-)-Triptophenolide and (+)-Triptolide.

Chemicals Related in the Paper:

Catalog Number Product Name Structure CAS Number Price
AP74285862 Triptophenolide Triptophenolide 74285-86-2 Price
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