Preparation of gamma-siloxyallyltributylstannanes and their use in the synthesis of (+/-)-1-deoxy-6,8a-di-epi-castanospermine.
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.
Chevallier
Floris
F
Laboratoire de Synthése Organique, Faculté des Sciences et des Techniques de Nantes, cedex France.
Le Grognec
Erwan
E
Beaudet
Isabelle
I
Fliegel
Florian
F
Evain
Michel
M
Quintard
Jean-Paul
JP