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. 2016 Feb 5;18(3):516-9.
doi: 10.1021/acs.orglett.5b03547. Epub 2016 Jan 13.

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

Mahipal Bodugam  1 , Salim Javed  1 , Arghya Ganguly  1 , Jessica Torres  1 , Paul R Hanson  1
Affiliations

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

Mahipal Bodugam et al. Org Lett. .

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.

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Figures

Figure 1
Figure 1
Natural Product Macrolactones Sch-725674 (1), Gloeosporone, 2 and Gliomasolides A–E, 3–7.
Scheme 1
Scheme 1
Synthesis Plan Toward Sch-725674, 1
Scheme 2
Scheme 2
Total Synthesis of Sch-725674, 1
See this image and copyright information in PMC

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