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

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...

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Bibliographic Details
Published in:Organic letters 2016-02, Vol.18 (3), p.516-519
Main Authors: Bodugam, Mahipal, Javed, Salim, Ganguly, Arghya, Torres, Jessica, Hanson, Paul R
Format: Article
Language:English
Subjects:
Antifungal Agents - chemical synthesis
Antifungal Agents - chemistry
Antifungal Agents - pharmacology
Catalysis
Hydrogenation
Macrolides - chemical synthesis
Macrolides - chemistry
Macrolides - pharmacology
Molecular Structure
Organophosphates
Stereoisomerism
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.5b03547