Modifications to the Synthesis of the Salvinorin A Carbon Skeleton
| Main Author: | |
|---|---|
| Language: | English |
| Published: |
The Ohio State University / OhioLINK
2016
|
| Subjects: | |
| Online Access: | http://rave.ohiolink.edu/etdc/view?acc_num=osu1462816273 |
| id |
ndltd-OhioLink-oai-etd.ohiolink.edu-osu1462816273 |
|---|---|
| record_format |
oai_dc |
| spelling |
ndltd-OhioLink-oai-etd.ohiolink.edu-osu14628162732021-08-03T06:36:39Z Modifications to the Synthesis of the Salvinorin A Carbon Skeleton Casbohm, Jerry S. Chemistry The mint, Salvia divinorum, has been used many years by the Mazatec Indians ofOaxaca, Mexico, for religious and medical purposes. Its hallucinogenic properties havecaptivated the interest of recreational drug users inspiring significant discussion of how tothe control it and other drugs. In 1982, Ortega reported the first isolation of salvinorin Afrom S. divinorum with a subsequent report from another independent isolation by theValdes group in 1984. Following its discovery, salvinorin A was found to be responsiblefor the hallucinogenic effects attributed to S. divinorum. This has characterizedsalvinorin A as the only non-nitrogenous hallucinogen and a selective ¿-opioid agonist.Its potent agonist properties have instilled significant interest from both biochemists andchemists.Herein are reported our efforts towards synthesizing salvinorin A. Difficulties indeveloping a scalable synthesis of the Diels-Alder precursor have been circumventedwith a copper mediated coupling. We have developed an intramolecular Diels-Alder/Tsuji allylation that diastereoselectively produces the salvinorin A trans-decalincore. Optimization of the post Tsuji allylation has been accomplished by changingvarious methods of deprotection and oxidations. 2016-09-01 English text The Ohio State University / OhioLINK http://rave.ohiolink.edu/etdc/view?acc_num=osu1462816273 http://rave.ohiolink.edu/etdc/view?acc_num=osu1462816273 unrestricted This thesis or dissertation is protected by copyright: all rights reserved. It may not be copied or redistributed beyond the terms of applicable copyright laws. |
| collection |
NDLTD |
| language |
English |
| sources |
NDLTD |
| topic |
Chemistry |
| spellingShingle |
Chemistry Casbohm, Jerry S. Modifications to the Synthesis of the Salvinorin A Carbon Skeleton |
| author |
Casbohm, Jerry S. |
| author_facet |
Casbohm, Jerry S. |
| author_sort |
Casbohm, Jerry S. |
| title |
Modifications to the Synthesis of the Salvinorin A Carbon Skeleton |
| title_short |
Modifications to the Synthesis of the Salvinorin A Carbon Skeleton |
| title_full |
Modifications to the Synthesis of the Salvinorin A Carbon Skeleton |
| title_fullStr |
Modifications to the Synthesis of the Salvinorin A Carbon Skeleton |
| title_full_unstemmed |
Modifications to the Synthesis of the Salvinorin A Carbon Skeleton |
| title_sort |
modifications to the synthesis of the salvinorin a carbon skeleton |
| publisher |
The Ohio State University / OhioLINK |
| publishDate |
2016 |
| url |
http://rave.ohiolink.edu/etdc/view?acc_num=osu1462816273 |
| work_keys_str_mv |
AT casbohmjerrys modificationstothesynthesisofthesalvinorinacarbonskeleton |
| _version_ |
1719440233877995520 |