Vinylogous Mukaiyama aldol reactions with 4-oxy-2-trimethylsilyloxypyrroles: relevance to castanospermine synthesis.

ABSTRACT:

Background

The diastereoselectivity of a vinylogous Mukaiyama aldol reaction of a series of N-substituted 4-oxy-2-trimethylsilyloxypyrroles with a tartrate-based aldehyde has been explored as a model reaction for castanospermine synthesis.

Results

The study has revealed that the reaction is sensitive to the nature of the combination of N- and 4-oxy substituents. With a N-PMB or N-Bn and 4-methoxy combination, the reaction generates an aldol adduct with the correct absolute configurations for C-8 and C-8a of the indolizidine alkaloid castanospermine. The adduct was transformed to an indolizidine, whose ketal could not be transformed appropriately for the target alkaloid.

Conclusion

The first successful diastereoselective Mukaiyama aldol strategy for the C-8 and C-8a st

SUBMITTER: Hunter R 

PROVIDER: S-EPMC2151077 | biostudies-literature | 2007 Nov

REPOSITORIES: biostudies-literature