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Modifications to the Synthesis of the Salvinorin A Carbon Skeleton

出版	Ohio State University, 2016
URL	http://books.google.com.hk/books?id=rHVQAQAACAAJ&hl=&source=gbs_api

註釋The mint, Salvia divinorum, has been used many years by the Mazatec Indians of Oaxaca, Mexico, for religious and medical purposes. Its hallucinogenic properties have captivated the interest of recreational drug users inspiring significant discussion of how to the control it and other drugs. In 1982, Ortega reported the first isolation of salvinorin A from S. divinorum with a subsequent report from another independent isolation by the Valdes group in 1984. Following its discovery, salvinorin A was found to be responsible for the hallucinogenic effects attributed to S. divinorum. This has characterized salvinorin A as the only non-nitrogenous hallucinogen and a selective k-opioid agonist. Its potent agonist properties have instilled significant interest from both biochemists and chemists. Herein are reported our efforts towards synthesizing salvinorin A. Difficulties in developing a scalable synthesis of the Diels-Alder precursor have been circumvented with a copper mediated coupling. We have developed an intramolecular Diels-Alder/Tsuji allylation that diastereoselectively produces the salvinorin A trans-decalin core. Optimization of the post Tsuji allylation has been accomplished by changing various methods of deprotection and oxidations.