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Enantioselective Synthesis of Some Nicotiana Alkaloids
Author(s) -
Mahboobi Siavosh,
Wiegrebe Wolfgang
Publication year - 1988
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.19883210314
Subject(s) - nornicotine , enantioselective synthesis , chemistry , formylation , alkaloid , stereochemistry , silyl ether , enol , nicotine , silylation , silyl enol ether , organic chemistry , catalysis , neuroscience , biology
A modified approach to myosmine ( 6 ) via a silyl enol ether of 3‐acetylpyridine ( 1 ) is described. Chiral reduction of 6 with N ‐(benzyloxycarbonyl)‐ L ‐proline/NaBH 4 and formylation leads to ( R )‐ N ‐formylnornicotine ( 8 ) (35 % ee) which in turn is converted to ( R )‐nornicotine ( 11 ) and ( R )‐nicotine ( 10 ).