Genre
- Journal Article
This paper describes a new general approach towards functionalized piperidine alkaloids, based on the stereo- and regioselective palladium(0)-catalyzed nucleophilic ring-opening of vinyl epoxides by nitrogen nucleophiles. The latter reaction provides access to stereo-defined and and syn aminoalcohol derivatives, 1-benzyloxy-5-(p-toluenesulfonamido)-3-alken-2-ols (5), which were transformed to (+)-pseudoconhydrine (3) and (+/-)-epi-pseudoconhydrine (9), respectively, via protection (silyl ether), hydrogenation, debenzylation and cyclization. Detosylation-deprotection gave the final products in good yields and high stereoisomeric purity. (C) 2000 Elsevier Science Ltd. All rights reserved.
Stockholm Univ, Arrhenius Lab, Dept Organ Chem, SE-10691 Stockholm, Sweden. Uppsala Univ, Dept Organ Chem, SE-75121 Uppsala, Sweden.; Backvall, JE, Stockholm Univ, Arrhenius Lab, Dept Organ Chem, SE-10691 Stockholm, Sweden.
OXFORD; THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND
PERGAMON-ELSEVIER SCIENCE LTD
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Source type: Electronic(1)
Language
- English
Subjects
- VENOM
- (+/-)-epi-pseudoconhydrine
- ACID
- DERIVATIVES
- ASYMMETRIC-SYNTHESIS
- (+)-pseudoconhydrine
- Chemistry, Organic
- RESOLUTION
- STEREOCONTROLLED ORGANOPALLADIUM ROUTE