Radical-mediated hydroalkylation of 2-vinylpyrrolidine derivatives: a versatile entry into indolizidine alkaloids

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 > Departement of Chemistry and Biochemistry

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:

23 Mar 2020 11:11

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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