Journal
CHEMICAL & PHARMACEUTICAL BULLETIN
Volume 67, Issue 1, Pages 64-70Publisher
PHARMACEUTICAL SOC JAPAN
DOI: 10.1248/cpb.c18-00718
Keywords
alkaloid; lactone; quaternary carbon; rearrangement; total synthesis
Funding
- Japan Society for the Promotion of Science (JSPS) [20002004, 22590002]
- Grants-in-Aid for Scientific Research [22590002] Funding Source: KAKEN
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An alternative synthetic route toward a key intermediate in the total synthesis of isoschizogamine is described. The Claisen-Johnson rearrangement stereoselectively constructed a quaternary carbon. Trifluo-roperacetic acid mediated the Baeyer-Villiger oxidation to form a bicyclic lactone. The Mukaiyama-Matsuo protocol converted the lactone into an alpha,beta-unsaturated lactone, that was used as the substrate for the rhodium-mediated 1,4-addition of an arylboronic acid.
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