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A Pot-Economical Approach to the Total Synthesis of Sch-725674.

ABSTRACT: A pot-economical total synthesis of antifungal Sch-725674, 1, is reported. The approach takes advantage of a number of one-pot, sequential transformations, including a phosphate tether-mediated one-pot, sequential RCM/CM/chemoselective hydrogenation protocol, a one-pot tosylation/acrylation sequence, and a one-pot, sequential Finkelstein reaction/Boord olefination/acetonide deprotection procedure to streamline the synthesis route by reducing isolation and purification procedures, thus saving time. Overall, an asymmetric route has been developed that is efficiently accomplished in seven pots from phosphate (S,S)-triene and with minimal purification.

SUBMITTER: Bodugam M

PROVIDER: S-EPMC4852165 | biostudies-literature | 2016 Feb

REPOSITORIES: biostudies-literature

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A Pot-Economical Approach to the Total Synthesis of Sch-725674.

Bodugam Mahipal M Javed Salim S Ganguly Arghya A Torres Jessica J Hanson Paul R PR

Organic letters 20160113 3

A pot-economical total synthesis of antifungal Sch-725674, 1, is reported. The approach takes advantage of a number of one-pot, sequential transformations, including a phosphate tether-mediated one-pot, sequential RCM/CM/chemoselective hydrogenation protocol, a one-pot tosylation/acrylation sequence, and a one-pot, sequential Finkelstein reaction/Boord olefination/acetonide deprotection procedure to streamline the synthesis route by reducing isolation and purification procedures, thus saving tim ...[more]

PMID: 26760683

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