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Synlett
DOI: 10.1055/a-2795-3115
DOI: 10.1055/a-2795-3115
Letter
A Practical and Efficient Asymmetric Synthesis of the Tobacco Natural Alkaloids (S)-Anatabine and (S)-Anabasine via an Allylation/Metathesis-based Approach
Authors
M-C. and M. A (Universidad de Murcia) thanks the Spanish Ministry of Science and Innovation: (Grants PID2019-106358GB-C22, and PID2020-113686GB-I00, MCIN/AEI/10.13039/501100011033) and to Fundación Séneca-CARM (Project 21907/PI/22) for financial support.
Supported by: Universidad de Murcia Supported by: Spanish Ministry of Science and Innovation MCIN/AEI/10.13039/501100011033,PID2019-106358GB-C22,PID2020-113686GB-I00
Dedication
Dedicated to Prof. Dr. Heinz Heimgartner
Abstract
A practical, concise, and high-yielding synthesis of enantiomerically pure anatabine and anabasine is described. Our approach is based on a highly diastereoselective indium-mediated addition of allyl bromide to enantiopure N-tert-butylsulfinyl aldimines and subsequent ring-closing metathesis followed by mild removal of the chiral auxiliary.
Keywords
Natural products - Synthesis of enantiomerically pure anatabine and anabasine - Ring closing methathesis - α-Heteroaryl piperidines - Enantiopure N-tert-butylsulfinyl aldiminesPublication History
Received: 03 December 2025
Accepted after revision: 22 January 2026
Article published online:
06 February 2026
© 2026. Thieme. All rights reserved.
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