Total synthesis of the indolizidine alkaloid tashiromine.

ABSTRACT:

Background

Tashiromine 1 is a naturally occurring indolizidine alkaloid. It has been the subject of thirteen successful total syntheses to date. Our own approach centres on the stereoselective construction of the indolizidine core by capture of an electrophilic acyliminium species by a pendant allylsilane. The key cyclisation precursor is constructed using olefin cross-metathesis chemistry, which has the potential to facilitate both racemic and asymmetric approaches, depending upon the choice of the allylsilane metathesis partner.

Results

The use of the allyltrimethylsilane cross-metathesis approach enables the rapid construction of the key cyclisation precursor 3 (3 steps from commercial materials), which undergoes acid-induced cyclisation to give the desired bicyclic indol

SUBMITTER: Marsden SP 

PROVIDER: S-EPMC2241604 | biostudies-literature | 2008 Jan

REPOSITORIES: biostudies-literature