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. 2019 Jan 21;9(5):2799-2802.
doi: 10.1039/c9ra00173e. eCollection 2019 Jan 18.

Enantioselective synthesis of anti-3-alkenyl-2-amido-3-hydroxy esters: application to the total synthesis of (+)-alexine

Lu Yu  1 , Peter Somfai  1
Affiliations

Enantioselective synthesis of anti-3-alkenyl-2-amido-3-hydroxy esters: application to the total synthesis of (+)-alexine

Lu Yu et al. RSC Adv. .

Abstract

A straightforward synthesis of anti-3-alkenyl-2-amido-3-hydroxy esters from the corresponding racemic α-amino-β-keto esters by using a ATH/DKR protocol has been developed. This method gives moderate to excellent yields with high chemo-, diastereo- and enantioselectivities for a broad range of substrates. In order to highlight the versatility of the methodology it was applied in an efficient asymmetric synthesis of the polyhydroxylated pyrrolizidine alkaloid (+)-alexine.

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Conflict of interest statement

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Figures

Scheme 1
Scheme 1. Proposed route from α-amido- β-keto ester 1 to polyhydroxylated pyrrolizidine and indolizidine alkaloids.
Scheme 2
Scheme 2. Retrosynthetic analysis of (+)-alexine.
Scheme 3
Scheme 3. Total synthesis of (+)-alexine.
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