Concise synthesis of piperarborenine B

Hui, C and Antonchick, AP ORCID: https://orcid.org/0000-0003-0435-9443, 2022. Concise synthesis of piperarborenine B. Bioorganic and Medicinal Chemistry, 67: 116817. ISSN 0968-0896

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Abstract

A concise synthesis of piperarborenine B is reported. Organocatalytic electrophilic amination of pyrrolidines, stereospecific oxidative ring contraction and an original diastereoselective Krapcho dealkoxycarbonylation/transmethylation contribute to a novel synthetic strategy to the preparation of a non-symmetrical cyclobutane core. Being transition-metal-free, directing-group-free and protecting-group-free, a five-step synthesis of piperarborenine B was accomplished.

Item Type:	Journal article
Publication Title:	Bioorganic and Medicinal Chemistry
Creators:	Hui, C. and Antonchick, A.P.
Publisher:	Elsevier BV
Date:	August 2022
Volume:	67
ISSN:	0968-0896
Identifiers:	Number Type 10.1016/j.bmc.2022.116817 DOI 1547770 Other
Divisions:	Schools > School of Science and Technology
Record created by:	Laura Borcherds
Date Added:	23 May 2022 09:45
Last Modified:	20 May 2023 03:00
URI:	https://irep.ntu.ac.uk/id/eprint/46347

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