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Title: Access to Enantiopure 5‑, 7‑, and 5,7-Substituted cis- Decahydroquinolines: Enantioselective Synthesis of (−)-Cermizine B
Author: Pinto, Alexandre
Griera Farres, Rosa
Molins i Grau, Elies
Fernández Cadenas, Israel
Bosch Cartes, Joan
Amat Tusón, Mercedes
Keywords: Alcaloides
Issue Date: 21-Mar-2017
Publisher: American Chemical Society
Abstract: Stereoconvergent cyclocondensation reactions of (R)- or (S)-phenylglycinol with appropriately substituted cyclohexanone-based δ-keto esters are the key steps of short synthetic routes to enantiopure 5-, 7-, and 5,7-substituted cisdecahydroquinolines. The factors governing the stereoselectivity of the cyclocondensation are discussed. The potential of the methodology is illustrated by a protecting-group-free synthesis of the phlegmarine-type Lycopodium alkaloid (-)-cermizine B.
Note: Versió postprint del document publicat a:
It is part of: Organic Letters, 2017, vol. 19, p. 1714-1717
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ISSN: 1523-7060
Appears in Collections:Articles publicats en revistes (Farmacologia, Toxicologia i Química Terapèutica)
Articles publicats en revistes (Institut de Biomedicina (IBUB))

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