Phosphate tether-mediated, one-pot, sequential protocols for the syntheses of 14-membered macrolactones Sch-725674 and 13-desmethyl-lyngbouilloside are reported. The key reactions involved in the synthesis of these molecules are one-pot, sequential RCM/CM/H<sub>2</sub>, Sharpless asymmetric epoxidation, Roskamp homologation, Boeckman acylketene cyclization and ring-closing metathesis. Our efficient, library amenable, step economical approach to assemble the 14-membered templates is also employed to synthesize simplified analogs, including sulfur- and phosphorus-based derivatives of both Sch-725674 and 13-Desmethyl-lyngbouilloside. Overall, the 14-membered macrolactone analogs contain three stereogenic centers and are obtained over a series of four one-pot, sequential processes starting from a common, readily-prepared triene phosphate triester, and requiring only four purification steps.

Phosphate tether-mediated, one-pot, sequential protocols for the synthesis of Sch725674, 13-desmethyl-lyngbouilloside and corresponding simplified analogs

251st National Meeting (2016)

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