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Synfacts 2011(9): 0925-0925  
DOI: 10.1055/s-0030-1260929
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of (±)-Aspidophylline A

Contributor(s): Steven V. Ley, Kimberley A. Roper
L. Zu, B. W. Boal, N. K. Garg*
University of California, Los Angeles, USA
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Publication History

Publication Date:
19 August 2011 (online)

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Significance

(±)-Aspidophylline A was isolated from the Apocynaceae family of plants and has been shown to reverse drug resistance in resistant KB cells. It is an indole alkaloid with a complex structure featuring a tricyclic furoindoline motif, highly substituted cyclohexyl ring, and a bridged [3.3.1] bicycle. The first total synthesis of this natural product was completed using an ‘interrupted Fischer indolization’, methodology previously developed by the Garg group (Org. Lett. 2009, 11, 3458), which could be used to install two rings in a one-pot process with complete diastereoselectivity.