Title:
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Access to Enantiopure 5‑, 7‑, and 5,7-Substituted cis- Decahydroquinolines: Enantioselective Synthesis of (−)-Cermizine B
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Author:
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Pinto, Alexandre; Griera Farres, Rosa; Molins i Grau, Elies; Fernández Cadenas, Israel; Bosch Cartes, Joan; Amat Tusón, Mercedes
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Other authors:
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Universitat de Barcelona |
Abstract:
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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. |
Subject(s):
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-Alcaloides -Lactames -Alkaloids -Lactams |
Rights:
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(c) American Chemical Society , 2017
info:eu-repo/semantics/embargoedAccess |
Document type:
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Article Article - Accepted version |
Published by:
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American Chemical Society
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