Ontology highlight
ABSTRACT:
SUBMITTER: Gotchev DB
PROVIDER: S-EPMC2527541 | biostudies-literature | 2006 Dec
REPOSITORIES: biostudies-literature
The Journal of organic chemistry 20061201 25
Two approaches to the aza-tricyclo dodecane skeleton of (-)-FR901483 are reported. Both routes utilized a Grignard addition to an N-acylpyridinium salt to establish the absolute stereochemistry at C-6 and a highly diastereoselective conjugate allylation reaction to form the quaternary center at C-1 of the natural product in an excellent yield. Although the desired polysubstituted piperidine intermediates were prepared regio- and stereoselectively, the construction of the C-8/C-9 bond connectivit ...[more]