Total synthesis of (-)-deglycocadambine
The first total synthesis of the monoterpene indole alkaloid (-)-deglycocadambine is achieved in 12 steps with (+)-genipin as the chiral starting material. The reported synthetic approach is characterized by an orchestrated cascade annulation between tryptamine and the highly functionalized dialdehy...
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sg-ntu-dr.10356-1809412024-11-08T15:32:18Z Total synthesis of (-)-deglycocadambine Wang, Fang-Xin Chen, Ying-Tao Liu, Hui Wang, Heng-Shan Liang, Hong Chen, Zhen-Feng Chi, Robin Yonggui School of Chemistry, Chemical Engineering and Biotechnology Chemistry Dialdehydes Oxazolidines The first total synthesis of the monoterpene indole alkaloid (-)-deglycocadambine is achieved in 12 steps with (+)-genipin as the chiral starting material. The reported synthetic approach is characterized by an orchestrated cascade annulation between tryptamine and the highly functionalized dialdehyde precursor, rapidly introducing the unique 6/5/6/7/6-fused pentacyclic skeleton and the ketone functional group at C19 in a convergent manner. The successful implementation of transannular oxidative cyclization at C3 for bridged oxazolidine formation in the late-stage synthetic campaign ensured the final total synthesis of this molecule. Ministry of Education (MOE) Nanyang Technological University National Research Foundation (NRF) Published version We are grateful for financial support from the National Natural Science Foundation of China (22201050, 21772029, 21801051, 21807091, 21961006, 22071036, and 22061007); the Natural Science Foundation of Guangxi Zhuang Autonomous Region (2024GXNSFAA010091 and 2023GXNSFBA026329); the Singapore National Research Foundation under its Competitive Research Program (NRF-CRP22-2019-0002); the Ministry of Education, Singapore, under its MOE AcRF Tier 1 Award (RG7/20 and RG5/19), MOE AcRF Tier 2 (MOE2019-T2-2- 117), Nanyang Technological University; the Frontiers Science Center for Asymmetric Synthesis and Medicinal Molecules, Department of Education, Guizhou Province [Qianjiaohe KY number (2020)004]; the 10 Talent Plan (Shicengci) of Guizhou Province ([2016]5649); the Science and Technology Department of Guizhou Province ([2018]2802 and [2019]1020); the State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources (CMEMR2022-A01); Guangxi Normal University; the Program of Introducing Talents of Discipline to Universities of China (111 Program, D20023) at Guizhou University; and Guizhou University. 2024-11-05T05:43:42Z 2024-11-05T05:43:42Z 2024 Journal Article Wang, F., Chen, Y., Liu, H., Wang, H., Liang, H., Chen, Z. & Chi, R. Y. (2024). Total synthesis of (-)-deglycocadambine. Organic Chemistry Frontiers, 11(17), 4869-4873. https://dx.doi.org/10.1039/d4qo01122h 2052-4129 https://hdl.handle.net/10356/180941 10.1039/d4qo01122h 2-s2.0-85199393302 17 11 4869 4873 en NRF-CRP22-2019-0002 RG7/20 RG5/19 MOE2019-T2-2-117 Organic Chemistry Frontiers © 2024 The Author(s). This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. application/pdf |
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Chemistry Dialdehydes Oxazolidines |
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Chemistry Dialdehydes Oxazolidines Wang, Fang-Xin Chen, Ying-Tao Liu, Hui Wang, Heng-Shan Liang, Hong Chen, Zhen-Feng Chi, Robin Yonggui Total synthesis of (-)-deglycocadambine |
| description |
The first total synthesis of the monoterpene indole alkaloid (-)-deglycocadambine is achieved in 12 steps with (+)-genipin as the chiral starting material. The reported synthetic approach is characterized by an orchestrated cascade annulation between tryptamine and the highly functionalized dialdehyde precursor, rapidly introducing the unique 6/5/6/7/6-fused pentacyclic skeleton and the ketone functional group at C19 in a convergent manner. The successful implementation of transannular oxidative cyclization at C3 for bridged oxazolidine formation in the late-stage synthetic campaign ensured the final total synthesis of this molecule. |
| author2 |
School of Chemistry, Chemical Engineering and Biotechnology |
| author_facet |
School of Chemistry, Chemical Engineering and Biotechnology Wang, Fang-Xin Chen, Ying-Tao Liu, Hui Wang, Heng-Shan Liang, Hong Chen, Zhen-Feng Chi, Robin Yonggui |
| format |
Article |
| author |
Wang, Fang-Xin Chen, Ying-Tao Liu, Hui Wang, Heng-Shan Liang, Hong Chen, Zhen-Feng Chi, Robin Yonggui |
| author_sort |
Wang, Fang-Xin |
| title |
Total synthesis of (-)-deglycocadambine |
| title_short |
Total synthesis of (-)-deglycocadambine |
| title_full |
Total synthesis of (-)-deglycocadambine |
| title_fullStr |
Total synthesis of (-)-deglycocadambine |
| title_full_unstemmed |
Total synthesis of (-)-deglycocadambine |
| title_sort |
total synthesis of (-)-deglycocadambine |
| publishDate |
2024 |
| url |
https://hdl.handle.net/10356/180941 |
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1816858923878055936 |