☆ 4.8 Article

Collective Total Synthesis of (-)-Lundurines A-C

ORGANIC LETTERS (2018)

Journal

ORGANIC LETTERS

Volume 20, Issue 6, Pages 1509-1512

Publisher

AMER CHEMICAL SOC

DOI: 10.1021/acs.orglett.8b00210

Keywords

-

Categories

Chemistry, Organic

Funding

NSFC [21732001, 21672017, 21472072, 21290183]
Shenzhen Science and Technology Innovation Committee [JCYJ20150529153646078, JSGG20160229150510483]
China Postdoctoral Science Foundation [2016M591003]
Program for Changjiang Scholars and Innovative Research Team in University [PCSIRT: IRT_15R28]
111 Program of MOE

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Abstract

A collective asymmetric total synthesis of lundurines A-C using L-pyroglutamic acid derived from the chiral pool is described. The key steps include a tandem reductive amination/lactamization sequence to introduce the pyrrolidinone ring, a palladium-catalyzed intramolecular direct C-H vinylation of indole to construct the crucial polyhydroazocine ring, and a Lewis acid promoted formal [3 + 2] cycloaddition/N-2 extrusion process to install the polysubstituted cyclopropyl ring.

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