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Issue 62, 2015
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Enantioselective syntheses of (R)-pipecolic acid, (2R,3R)-3-hydroxypipecolic acid, β-(+)-conhydrine and (−)-swainsonine using an aziridine derived common chiral synthon

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Abstract

Concise total syntheses of (R)-pipecolic acid, (R)-ethyl-6-oxopipecolate, (2R,3R)-3-hydroxypipecolic acid and formal syntheses of β-(+)-conhydrine, (−)-lentiginosine, (−)-swainsonine and 1,2-di-epi-swainsonine have been accomplished starting from a common chiral synthon. The present strategy employs regioselective aziridine ring opening, Wittig olefination and RCM as the key chemical transformations.

Graphical abstract: Enantioselective syntheses of (R)-pipecolic acid, (2R,3R)-3-hydroxypipecolic acid, β-(+)-conhydrine and (−)-swainsonine using an aziridine derived common chiral synthon

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Publication details

The article was received on 10 Apr 2015, accepted on 26 May 2015 and first published on 26 May 2015


Article type: Paper
DOI: 10.1039/C5RA06429E
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RSC Adv., 2015,5, 50580-50590

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    Enantioselective syntheses of (R)-pipecolic acid, (2R,3R)-3-hydroxypipecolic acid, β-(+)-conhydrine and (−)-swainsonine using an aziridine derived common chiral synthon

    S. P. Chavan, L. B. Khairnar, K. P. Pawar, P. N. Chavan and S. A. Kawale, RSC Adv., 2015, 5, 50580
    DOI: 10.1039/C5RA06429E

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