Access to Enantiopure 5‑, 7‑, and 5,7-Substituted cis-Decahydroquinolines: Enantioselective Synthesis of (−)-Cermizine B

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 cis-decahydro­quinolines. The factors governing the stereoselectivity of...

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Bibliographic Details
Published in:Organic letters 2017-04, Vol.19 (7), p.1714-1717
Main Authors: Pinto, Alexandre, Griera, Rosa, Molins, Elies, Fernández, Israel, Bosch, Joan, Amat, Mercedes
Format: Article
Language:English
Subjects:
Alcaloides
Alkaloids
Lactames
Lactams
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Summary: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 cis-decahydro­quinolines. 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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.7b00492