Suravarapu, Sankar Rao; Peter, Bettina; Renaud, Philippe (2019). Radical-mediated hydroalkylation of 2-vinylpyrrolidine derivatives: a versatile entry into indolizidine alkaloids. Science China Chemistry, 62(11), pp. 1504-1506. Springer 10.1007/s11426-019-9598-1
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A concise route for the preparation of two simple optically pure indolizidin-5-ones has been developed. The key chain elongation process was achieved using a triethylborane/catechol mediated hydroalkylation of Boc-protected 2-vinylpyrrolidines. By using complementary strategies, these two bicyclic lactams can be alkylated with complete control of the stereochemistry at C(5) and their conversion to a variety of indolizidine alkaloids such as coniceine, indolizidine 209D and 167B, 5-epi-indolizidine 249A and monomorine has been reported in the literature.
Item Type: |
Journal Article (Original Article) |
|---|---|
Division/Institute: |
08 Faculty of Science > Department of Chemistry, Biochemistry and Pharmaceutical Sciences (DCBP) |
UniBE Contributor: |
Renaud, Philippe |
Subjects: |
500 Science > 570 Life sciences; biology 500 Science > 540 Chemistry |
ISSN: |
1674-7291 |
Publisher: |
Springer |
Language: |
English |
Submitter: |
Franziska Bornhauser-Rufer |
Date Deposited: |
06 Feb 2020 15:33 |
Last Modified: |
05 Dec 2022 15:35 |
Publisher DOI: |
10.1007/s11426-019-9598-1 |
BORIS DOI: |
10.7892/boris.138847 |
URI: |
https://boris.unibe.ch/id/eprint/138847 |
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