Convergent Synthesis of Fully Functionalized Ring C Allocolchicinoids. Benzannulation Approach

A novel convergent approach to fully functionalized ring C allocolchicinoids is developed which is based on the benzannulation reaction of Fischer carbene complexes with alkynes. The efficacy of this strategy was established with the conversion of bromide 1a (R1 = Me, R2 = H) to the biaryl phenol 3a...

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Bibliographic Details
Published in:Organic letters 2001-08, Vol.3 (17), p.2641-2644
Main Authors: Vorogushin, Andrei V, Wulff, William D, Hansen, Hans-Jürgen
Format: Article
Language:English
Subjects:
Colchicine - analogs & derivatives
Colchicine - chemical synthesis
Stereoisomerism
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Summary:A novel convergent approach to fully functionalized ring C allocolchicinoids is developed which is based on the benzannulation reaction of Fischer carbene complexes with alkynes. The efficacy of this strategy was established with the conversion of bromide 1a (R1 = Me, R2 = H) to the biaryl phenol 3a (R = Me, RL = Pr, RS = H) via the carbene complex 2a. Bromide 1b (R1 = t-Bu, R2 = OMe) was then used for the analogous preparation of the diastereomeric allocolchicinoids 3b (R = Me, RL = Pr, RS = H).
ISSN:1523-7060
1523-7052
DOI:10.1021/ol0100881