Transition-metal-free stereoselective synthesis of C(1)–C(6) fragment of epothilones and their structural analogues

Add time:07/31/2019    Source:sciencedirect.com

Two efficient and scalable asymmetric syntheses of C(1)–C(6) fragment of epothilones and their structural analogues from commercially available 1,2:5,6-di-O-isopropylidene-d-mannitol have been performed in seven and 12 steps with 35% and 36% overall yields, respectively. Both the approaches include of one-pot, sequential transformations. The key steps are l-histidine-catalyzed aldol reaction, Barton–McCombie deoxygenation, zinc-mediated Vasella fragmentation, and oxidative nitrile synthesis.

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