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Synthesis of New Allocolchicinoids with Seven- and Eight-Membered B-Rings by Enyne Ring-Closing Metathesis

✍ Scribed by François-Didier Boyer; Issam Hanna

Publisher
John Wiley and Sons
Year
2008
Tongue
English
Weight
349 KB
Volume
2008
Category
Article
ISSN
1434-193X

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✦ Synopsis

Abstract

Total syntheses of allocolchicines 4 and 5, with the ester functionality in the C‐ring at the C10 or C11 positions, is reported. An asymmetric synthesis of (7__S__)‐allocolchicine 5 is also described. The main features included the elaboration of a common intermediate, the AB bicyclic ring system, in which the construction of the seven‐membered ring was achieved by an enyne ring‐closing metathesis (RCM) reaction. A subsequent Diels–Alder/aromatization sequence afforded the set of functionalized ring‐C allocolchicinoids with high regioselectivity. This strategy was also applied for the synthesis of allocolchicine 6, containing an eight‐membered B‐ring.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

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