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Synfacts 2020; 16(11): 1272
DOI: 10.1055/s-0040-1706317
Synthesis of Natural Products and Potential Drugs

Total Synthesis of (±)-Ginkgolide B

Contributor(s):
Erick M. Carreira
,
Felix Pultar
Crimmins MT, *, Pace JM, Nantermet PG, Kim-Meade AS, Thomas JB, Watterson SH, Wagman AS. University of North Carolina at Chapel Hill, USA
The Total Synthesis of (±)-Ginkgolide B.

J. Am. Chem. Soc. 2000;
122: 8453-8463
DOI: 10.1021/ja001747s.
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Key words

(±)-ginkgolide B - [2+2] cycloaddition - homoenolate - oxidative fragmentation

Significance

Ginkgolide B is a diterpenoid isolated from Ginkgo biloba. The structural complexity and the biological properties of this natural product have fascinated chemists for decades.


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Comment

Zinc homoenolate conjugate addition to A followed by cyclization yielded enone C. Conformational analysis led the authors to the discovery of a high-yielding photocycloaddition. Oxidative fragmentation and furan installation granted access to this intriguing molecule.


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Publication History

Article published online:
20 October 2020

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