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Expeditious Enantioselective Biomimetic Synthesis of the Nitraria Alkaloids (+)‐Isonitramine and (−)‐Sibirine
Author(s) -
François David,
Lallemand MarieChristine,
Selkti Mohamed,
Tomas Alain,
Kunesch Nicole,
Husson HenriPhilippe
Publication year - 1998
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/(sici)1521-3773(19980202)37:1/2<104::aid-anie104>3.0.co;2-k
Subject(s) - enantioselective synthesis , chirality (physics) , glutaraldehyde , biomimetic synthesis , chemistry , stereochemistry , total synthesis , combinatorial chemistry , organic chemistry , catalysis , physics , chiral symmetry breaking , quantum mechanics , nambu–jona lasinio model , quark
The reaction of glutaraldehyde with ( R )‐ or ( S )‐phenylglycinol as the source of nitrogen and the chirality inductor directly provides the spiropiperidine skeleton [Eq. (a)] of the alkaloids sibirine and isonitramine. The title compounds are available in a total of three and four steps, respectively.