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Total synthesis of 8,14-dihydromorphinandienone alkaloids

Organic Letters, ISSN: 1523-7052, Vol: 16, Issue: 6, Page: 1708-1711
2014
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Article Description

A collective synthesis of 8,14-dihydronorsalutaridine, 8,14- dihydrosalutaridine, norisosinomenine, and isosinomenine is reported. The strategy provides direct access to the correct oxidation level of the products. The combination of an organocatalyst guanidine superbase, a tertiary amine base, and a dehydrating agent was necessary for the successful Henry-Michael- dehydration cascade to form the phenanthrene motif. The required selective aliphatic nitro reduction could only be achieved under heterogeneous transfer-hydrogenation conditions. © 2014 American Chemical Society.

Bibliographic Details

Ghavimi, Bahman; Magnus, Philip

American Chemical Society (ACS)

Biochemistry, Genetics and Molecular Biology; Chemistry

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