title: Preparation of gamma-siloxyallyltributylstannanes and their use in the synthesis of (+/-)-1-deoxy-6,8a-di-epi-castanospermine.
abstract: gamma-siloxyallyltributylstannanes were selectively obtained as E or Z isomers from beta-tributylstannylacrolein upon reaction with lithium or magnesium alkylcyanocuprates. The ability of the reagents to give a high syn selectivity when added to iminium salts has been used for the efficient synthesis of (+/-)-1-deoxy-6,8a-di-epi-castanospermine from succinimide. The key step of the synthesis was the allylstannation of the N-allyliminium intermediate followed by ring closing metathesis.
authors.affiliation: Laboratoire de Synthése Organique, Faculté des Sciences et des Techniques de Nantes, cedex France.
authors.forename: Floris
authors.initials: F
authors.lastname: Chevallier
authors.forename: Erwan
authors.initials: E
authors.lastname: Le Grognec
authors.forename: Isabelle
authors.initials: I
authors.lastname: Beaudet
authors.forename: Florian
authors.initials: F
authors.lastname: Fliegel
authors.forename: Michel
authors.initials: M
authors.lastname: Evain
authors.forename: Jean-Paul
authors.initials: JP
authors.lastname: Quintard