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Synfacts 2006(12): 1194-1194  
DOI: 10.1055/s-2006-955598
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (-)-Nigellamine A2

Contributor(s): Philip Kocienski, Fiona Black
J. Bian, M. Van Wingerden, J. M. Ready*
The University of Texas Southwestern Medical Center at Dallas, USA
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Publication History

Publication Date:
22 November 2006 (online)

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Significance

(-)-Nigellamine A2 is a dolabellane diterpene isolated from Nigella sativa. The isopropylidene cyclopentane ring, containing the C-11 stereocenter, was synthesized using an intramolecular Pd-catalyzed allylic alkylation of malonate A. A Nozaki-Hiyama-Kishi cyclization proceeded in good yield and high diastereoselectivity to construct the 11-membered ring. The synthesis depicted gives the enantiomer of the natural product.