Tetrahedron Letters p. 6139 - 6142 (1998)
Update date:2022-09-26
Topics:
Py, Sandrine
Harwig, Curtis W.
Banerjee, Srabani
Brown, David L.
Fallis, Alex G.
The synthesis of the bicyclic enediyne compounds 14-18 is described. The bicyclo[7.3.1]trideca-4,9-dien-2,6-diynes (21) are calicheamicin-taxoid mimics, that possess the Taxotere side chain and an enediyne core. Cyclization of the iodo-aldehyde 13 [CrCl2(THF)2] afforded the bicyclic alcohol 14 as a single diastereomer (76%) and allylic oxidation (SeO2) followed by reaction with the oxazolidine intermediate 19, resolution and hydrolysis provided the taxamycins 21.
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