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Synthesis 2022; 54(06): 1577-1586
DOI: 10.1055/a-1681-4067
DOI: 10.1055/a-1681-4067
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A Flexible Approach to the Synthesis of Type II and III Lepadin Alkaloids
This work was supported by grants from the National Natural Science Foundation of China (21172153, 22171190), the Sichuan Science and Technology Program (2019YJ0032) and the Fundamental Research Funds for the Central Universities.
Abstract
A flexible approach to both type II and III lepadin alkaloids is developed for the first time. A key Diels–Alder reaction based on a novel chiral ketolactone dienophile is employed to obtain the desirable all-cis-trisubstituted cyclohexene with excellent regio- and stereoselectivity. As the subsequent closure of the piperidine ring is devised at the N1 and C2 position via an intramolecular nucleophilic amination, the two stereochemical types of lepadin frameworks with the opposite configuration at C2 can be conveniently accessible from a common intermediate. By the approach, lepadins D, E (type II) and F (type III) are stereoselectively synthesized from ethyl l-lactate.
Key words
lepadin - alkaloid - total synthesis - stereoselective synthesis - ketolactone dienophile - Diels–Alder reactionSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1681-4067.
- Supporting Information
Publication History
Received: 24 September 2021
Accepted after revision: 28 October 2021
Accepted Manuscript online:
28 October 2021
Article published online:
16 December 2021
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