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Abstract
The natural product peloruside A, a 16-membered macrolide antitumor agent, was isolated from a marine sponge in New Zealand in 1999. It exhibits microtubule-stabilizing activity in the treatment of cancer cells. This anti-cancer activity is similar to the effect of paclitaxel (Taxol®), a well developed and commercially available drug in cancer treatments.
Peloruside A represents a new class of antitumor agents with significant clinical potential. The intriguing structure, very low natural abundance, and clinical potential of peloruside A has attracted immense synthetic interest. Thus far, De Brabander et al., Taylor et al. and subsequently Ghosh and co-workers have achieved the total synthesis of peloruside A. Furthermore, a number of synthetic studies of peloruside A subunits have been reported.
Herein we report a convergent synthesis of an analogue of the C1-C11 fragment. The key steps involve 1,3-dithiane coupling reactions and a stereoselective Mukaiyama aldol reaction.
