An enantioselective total syntfiesis of (-)-FR182877 is described. This total synthesis features 1) the one-pot stereoselective tandem IMDA-IMHDA reaction which affords the tetracyclic compound including the ABCD ring system of (-)-FR182877 with the correct new seven stereogenie centers, 2) the palladium-mediated 7-exo-trig intramolecular Heck reaction for the construction of the highly strained seven-membefed F-ring, and 3) the iridium-mediated isomerization of the allylic alcohol to the a-methyl ketone followed by epimerization and the stereoselective reduction to furnish all the stereogenic centers of (-)-FR182877.
|ジャーナル||Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry|
|出版ステータス||Published - 2011 6 1|
ASJC Scopus subject areas
- Organic Chemistry