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; Thorsten Bach

doi:10.1055/a-1464-2576

Synthesis, Table of Contents

Synthesis 2021; 53(22): 4246-4262
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

,

Thorsten Bach ∗

Abstract

All articles of this category

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 synthesis

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References

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