The development of novel methods for the facile and streamlined synthesis of antifungal natural product Sch-725674 and (–)-13-desmethyl-lyngbouilloside is reported. The key reactions involved in syntheses of these small molecules are one-pot sequential, iterative RCM/CM/chemoselective hydrogenation, Finkelstein reaction, Boord olefination, ring-closing metathesis, Roskamp homologation and Boeckman acylketene cyclization. These efficient, pot-economical and library amenable approaches are further extended for the facile syntheses of diverse range of α,β-unsaturated C-, S-, P-containing macrocyclclic analogs of Sch-725674, (+)-neopeltolide and lyngbouilloside. These novel, structurally and stereochemically attenuated macrocycles will be submitted to our collaborators for biological evaluations.

Efficient synthesis of 1,3-anti-diol containing bioactive natural products and corresponding analogs via modular, pot-economical and library amenable protocols

255th National Meeting (2018)

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