Synthesis
DOI: 10.1055/a-1464-2576
special topic
Special Issue dedicated to Prof. Sarah Reisman, recipient of the 2019 Dr. Margaret Faul Women in Chemistry Award

Studies towards the Synthesis of (–)-Pulvomycin: Construction of the C12–C40 Segment by a Stereoselective Aldol Reaction

Sebastian Wienhold
,
Lukas Fritz
,
Tatjana Judt
,
Sabrina Hackl
,
Thomas Neubauer
,
Bastian Sauerer
,
Financial support by the Deutsche Forschungsgemeinschaft (Ba 1372/18) is gratefully acknowledged. S.W. was supported by a Ph.D. fellowship of the Fonds der Chemischen Industrie, T.N. was the recipient of a Ph.D. scholarship by the Studienstiftung des Deutschen Volkes.


Abstract

A convergent strategy was developed for the synthesis of the C12–C40 segment of (–)-pulvomycin. Key step was a diastereoselective aldol reaction between a chiral ethyl ketone representing the C24–C40 fragment and a chiral aldehyde representing the C12–C23 fragment. Both compounds were prepared from enantiomerically pure building blocks in a convergent fashion. The longest linear sequence commenced with a known d-fucose-derived glycosyl donor and entailed a total number of 16 steps. The desired anti-aldol product was obtained in a total yield of 5% over these steps and contains 12 out of 13 stereogenic centers present in the natural product.

Supporting Information

Primary Data



Publication History

Received: 19 March 2021

Accepted: 25 March 2021

Publication Date:
25 March 2021 (online)

© 2021. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 
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