Studies toward the First Stereoselective Total Synthesis of (±)-Quinolizidine 195C and Other Transformations
Starting from a thio-substituted 4-quinolizidinone, a series of C-6 alkylated derivatives with a trans C-6, C-9a relationship was synthesized. Further transformations led to the first stereoselective total synthesis of the structure proposed for (±)-quinolizidine 195C, the major alkaloid isolated fr...
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| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2013-07-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/18/7/8243 |
| _version_ | 1828472977411276800 |
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| author | Shang-Shing P. Chou Jhih-Liang Huang |
| author_facet | Shang-Shing P. Chou Jhih-Liang Huang |
| author_sort | Shang-Shing P. Chou |
| collection | DOAJ |
| description | Starting from a thio-substituted 4-quinolizidinone, a series of C-6 alkylated derivatives with a trans C-6, C-9a relationship was synthesized. Further transformations led to the first stereoselective total synthesis of the structure proposed for (±)-quinolizidine 195C, the major alkaloid isolated from the skin extracts of the Madagascan frog Mantella betsileo. Since the spectral data of the synthetic and natural products differed significantly, the true structure of (±)-quinolizidine 195C remains uncertain. |
| first_indexed | 2024-12-11T05:37:39Z |
| format | Article |
| id | doaj.art-f9d1c0f1fcd54d5ab7301bc226c6a1c8 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-11T05:37:39Z |
| publishDate | 2013-07-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-f9d1c0f1fcd54d5ab7301bc226c6a1c82022-12-22T01:19:14ZengMDPI AGMolecules1420-30492013-07-011878243825610.3390/molecules18078243Studies toward the First Stereoselective Total Synthesis of (±)-Quinolizidine 195C and Other TransformationsShang-Shing P. ChouJhih-Liang HuangStarting from a thio-substituted 4-quinolizidinone, a series of C-6 alkylated derivatives with a trans C-6, C-9a relationship was synthesized. Further transformations led to the first stereoselective total synthesis of the structure proposed for (±)-quinolizidine 195C, the major alkaloid isolated from the skin extracts of the Madagascan frog Mantella betsileo. Since the spectral data of the synthetic and natural products differed significantly, the true structure of (±)-quinolizidine 195C remains uncertain.http://www.mdpi.com/1420-3049/18/7/8243aza-Diels-Alder reactionintramolecular aza-Michael reactionquinolizidinesquinolizidine 195C |
| spellingShingle | Shang-Shing P. Chou Jhih-Liang Huang Studies toward the First Stereoselective Total Synthesis of (±)-Quinolizidine 195C and Other Transformations Molecules aza-Diels-Alder reaction intramolecular aza-Michael reaction quinolizidines quinolizidine 195C |
| title | Studies toward the First Stereoselective Total Synthesis of (±)-Quinolizidine 195C and Other Transformations |
| title_full | Studies toward the First Stereoselective Total Synthesis of (±)-Quinolizidine 195C and Other Transformations |
| title_fullStr | Studies toward the First Stereoselective Total Synthesis of (±)-Quinolizidine 195C and Other Transformations |
| title_full_unstemmed | Studies toward the First Stereoselective Total Synthesis of (±)-Quinolizidine 195C and Other Transformations |
| title_short | Studies toward the First Stereoselective Total Synthesis of (±)-Quinolizidine 195C and Other Transformations |
| title_sort | studies toward the first stereoselective total synthesis of quinolizidine 195c and other transformations |
| topic | aza-Diels-Alder reaction intramolecular aza-Michael reaction quinolizidines quinolizidine 195C |
| url | http://www.mdpi.com/1420-3049/18/7/8243 |
| work_keys_str_mv | AT shangshingpchou studiestowardthefirststereoselectivetotalsynthesisofquinolizidine195candothertransformations AT jhihlianghuang studiestowardthefirststereoselectivetotalsynthesisofquinolizidine195candothertransformations |