CC BY-ND-NC 4.0 · SynOpen 2019; 03(01): 26-35
DOI: 10.1055/s-0037-1611665
paper
Copyright with the author

Stereoselective Total Synthesis of Macrolide Sch-725674 and C-7-epi-Sch-725674

Karunakar Baikadi
,
Anil Talakokkula
,
A. Venkat Narsaiah*
Organic Synthesis Laboratory, Fluoro-Agrochemicals Department, CSIR-Indian Institute of Chemical Technology, Hyderabad, 500007, Telangana, India   Email: vnakkirala2001@yahoo.com   Email: vnakkirala@csiriict.in
› Author Affiliations
K.B. and A.T. are grateful to CSIR-New Delhi and UGC-New Delhi, ­respectively, for providing Fellowships, and the Minister of Science and Technology for providing financial support under DST-SERB-GAP-0563.
Further Information

Publication History

Received: 12 December 2018

Accepted after revision: 09 January 2019

Publication Date:
26 February 2019 (online)

Abstract

The stereoselective total synthesis of Sch-725674 in 14 ­linear synthetic steps with 10.3% overall yield is described. The synthesis started from commercially available starting materials, d-ribose and (R)-benzyl glycidol. The key reactions involved CBS reduction, Julia–­Kocienski olefination, Horner–Wadsworth–Emmons reaction, and ­Shiina macrolactonization.

Supporting Information

 
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