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A concise enantioselective synthesis of the AB ring system of the manzamine alkaloids by ring-closing enyne metathesis

✍ Scribed by J.Stephen Clark; Robert J Townsend; Alexander J Blake; Simon J Teat; Amanda Johns

Publisher
Elsevier Science
Year
2001
Tongue
French
Weight
84 KB
Volume
42
Category
Article
ISSN
0040-4039

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✦ Synopsis

The AB ring system found in the manzamine A and related alkaloids has been prepared from (-)-quinine by a short enantioselective route. The key step in the sequence is a ruthenium-catalysed ring-closing enyne metathesis re action which delivers a bicyclic diene in good yield. The functionality required for further elaboration of the AB system has been installed by sequential regioselective hydroboration and stereoselective catalytic aminohydroxylation.

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Generous financial support by the MPG, the Fonds der Chemischen Industrie, and the Merck Research Council is gratefully acknowledged. We thank Dr. D. De Souza for helpful comments and discussions and Dipl.-Chem. J. T. Jensen for preliminary experiments on the synthesis of the acid segment.