Synthesis of an isomer of lycoplanine a via cascade cyclization to construct the spiro-N,O-acetal moiety
An isomer of lycoplanine A with a 6/10/5/5 tetracyclic skeleton was synthesized using D–A reaction and cascasde reaction to respectively construct the [9.2.2] pentadecane skeleton and the challenging 1-oxa-6-azaspiro[4.4]nonane spirocenter. Morever, detailed DFT calculations were conducted to explai...
| Main Authors: | , , , , , , |
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| Format: | Article |
| Language: | English |
| Published: |
2021
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| Online Access: | https://eprints.nottingham.ac.uk/64854/ |
| _version_ | 1848800175463596032 |
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| author | Gao, Weiwei Wang, Xiaodong Yao, Linbin Tang, Bencan Mu, Guohao Shi, Tao Wang, Zhen |
| author_facet | Gao, Weiwei Wang, Xiaodong Yao, Linbin Tang, Bencan Mu, Guohao Shi, Tao Wang, Zhen |
| author_sort | Gao, Weiwei |
| building | Nottingham Research Data Repository |
| collection | Online Access |
| description | An isomer of lycoplanine A with a 6/10/5/5 tetracyclic skeleton was synthesized using D–A reaction and cascasde reaction to respectively construct the [9.2.2] pentadecane skeleton and the challenging 1-oxa-6-azaspiro[4.4]nonane spirocenter. Morever, detailed DFT calculations were conducted to explain the selectivity in the D–A reaction. This study may provide sufficient experience for the total synthesis of lycoplanine A and other alkaloids with similar spiro-N,O-acetal cores. |
| first_indexed | 2025-11-14T20:47:23Z |
| format | Article |
| id | nottingham-64854 |
| institution | University of Nottingham Malaysia Campus |
| institution_category | Local University |
| language | English |
| last_indexed | 2025-11-14T20:47:23Z |
| publishDate | 2021 |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | nottingham-648542021-03-24T02:29:16Z https://eprints.nottingham.ac.uk/64854/ Synthesis of an isomer of lycoplanine a via cascade cyclization to construct the spiro-N,O-acetal moiety Gao, Weiwei Wang, Xiaodong Yao, Linbin Tang, Bencan Mu, Guohao Shi, Tao Wang, Zhen An isomer of lycoplanine A with a 6/10/5/5 tetracyclic skeleton was synthesized using D–A reaction and cascasde reaction to respectively construct the [9.2.2] pentadecane skeleton and the challenging 1-oxa-6-azaspiro[4.4]nonane spirocenter. Morever, detailed DFT calculations were conducted to explain the selectivity in the D–A reaction. This study may provide sufficient experience for the total synthesis of lycoplanine A and other alkaloids with similar spiro-N,O-acetal cores. 2021-02-02 Article PeerReviewed application/pdf en cc_by https://eprints.nottingham.ac.uk/64854/1/Synthesis%20of%20an%20isomer%20of%20lycoplanine%20Aviacascade%20cyclization%20to%20construct%20the%20spiro-N%2CO-acetal%20moiety_submitted%20version.pdf Gao, Weiwei, Wang, Xiaodong, Yao, Linbin, Tang, Bencan, Mu, Guohao, Shi, Tao and Wang, Zhen (2021) Synthesis of an isomer of lycoplanine a via cascade cyclization to construct the spiro-N,O-acetal moiety. Organic & Biomolecular Chemistry, 19 (8). pp. 1748-1751. ISSN 1477-0520 http://dx.doi.org/10.1039/D0OB02399J doi:10.1039/D0OB02399J doi:10.1039/D0OB02399J |
| spellingShingle | Gao, Weiwei Wang, Xiaodong Yao, Linbin Tang, Bencan Mu, Guohao Shi, Tao Wang, Zhen Synthesis of an isomer of lycoplanine a via cascade cyclization to construct the spiro-N,O-acetal moiety |
| title | Synthesis of an isomer of lycoplanine a via cascade cyclization to construct the spiro-N,O-acetal moiety |
| title_full | Synthesis of an isomer of lycoplanine a via cascade cyclization to construct the spiro-N,O-acetal moiety |
| title_fullStr | Synthesis of an isomer of lycoplanine a via cascade cyclization to construct the spiro-N,O-acetal moiety |
| title_full_unstemmed | Synthesis of an isomer of lycoplanine a via cascade cyclization to construct the spiro-N,O-acetal moiety |
| title_short | Synthesis of an isomer of lycoplanine a via cascade cyclization to construct the spiro-N,O-acetal moiety |
| title_sort | synthesis of an isomer of lycoplanine a via cascade cyclization to construct the spiro-n,o-acetal moiety |
| url | https://eprints.nottingham.ac.uk/64854/ https://eprints.nottingham.ac.uk/64854/ https://eprints.nottingham.ac.uk/64854/ |