Tetrahedron letters

Taxamycin studies: Synthesis of taxoid-calicheamicin hybrids

S Py, CW Harwig, S Banerjee, DL Brown, AG Fallis

Index: Py, Sandrine; Harwig, Curtis W.; Banerjee, Srabani; Brown, David L.; Fallis, Alex G. Tetrahedron Letters, 1998 , vol. 39, # 34 p. 6139 - 6142

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Citation Number: 33

Abstract

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 ...