Chemistry Department, University of Alberta, Edmonton, Alberta T6G 2G2, Canada. derrick.clive@ualberta.ca
The Journal of organic chemistry 2001 Jul 13Acetylenic alcohol 10 was converted successively into silane 11 and phenylseleno carbonate 14. On treatment with Ph3SnH, the latter underwent 5-exo-digonal radical cyclization, intramolecular hydrogen transfer, and 5-endo-trigonal cyclization, yielding 15. Conversion of the lactone into the lactol benzyl ether 17, carbon-silicon bond cleavage, and regeneration of the lactone carbonyl gave (+)-juruenolide C (1).
D L Clive, E S Ardelean. Synthesis of (+)-juruenolide c: use of sequential 5-exo-digonal radical cyclization, 1,5-intramolecular hydrogen transfer, and 5-endo-trigonal cyclization. The Journal of organic chemistry. 2001 Jul 13;66(14):4841-4
PMID: 11442414
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