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J Am Chem Soc. 2012 May 16;134(19):8078-81. doi: 10.1021/ja302765m. Epub 2012 May 2.

Total syntheses of anominine and tubingensin A.

Author information

1
State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.

Abstract

A divergent strategy for the total syntheses of the indole terpenoid anominine (1) and its natural congener tubingensin A (2) has been developed. The common intermediate 11 bearing all of the required stereogenic centers for both natural products was first assembled by employing a Ueno-Stork radical cyclization and a Sc(OTf)(3)-mediated Mukaiyama aldol reaction to form the key C-C bonds in a stereocontrolled manner. The route to anominine features a radical deoxygenation followed by an efficient side-chain installation, while the path to tubingensin A exploits a CuOTf-promoted 6π-electrocyclization/aromatization sequence to forge the central region of the pentacyclic scaffold.

PMID:
22537293
DOI:
10.1021/ja302765m
[Indexed for MEDLINE]

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