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Synthesis 2021; 53(22): 4246-4262
DOI: 10.1055/a-1464-2576
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
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.
Key words
aldol reaction - alkenes - diastereoselectivity - natural products - polyketides - total synthesisSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1464-2576.
- Supporting Information
Primary Data
- Primary Data
Primary data for this article are available online at https://zenodo.org/record/4637081 and can be cited using the following DOI: 10.5281/zenodo.4637081.
Publication History
Received: 19 March 2021
Accepted: 25 March 2021
Accepted Manuscript online:
25 March 2021
Article published online:
15 April 2021
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