Issue 9, 2022

Efficient synthesis of tetracyclic γ-lactams via gold-catalyzed oxidative cyclization of alkenyl diynes

Abstract

An efficient gold-catalyzed cascade cyclization of alkenyl diynes involving alkyne oxidation, carbene-alkyne metathesis and cyclopropanation has been developed, furnishing a series of tetracyclic γ-lactams bearing one quaternary carbon center and one tertiary carbon center in moderate to good yields with excellent diastereoselectivities. In addition, the proposed mechanistic rationale for this oxidative cyclization is well supported by theoretical calculations.

Graphical abstract: Efficient synthesis of tetracyclic γ-lactams via gold-catalyzed oxidative cyclization of alkenyl diynes

Supplementary files

Article information

Article type
Research Article
Submitted
24 Jan 2022
Accepted
26 Mar 2022
First published
30 Mar 2022

Org. Chem. Front., 2022,9, 2557-2562

Efficient synthesis of tetracyclic γ-lactams via gold-catalyzed oxidative cyclization of alkenyl diynes

C. Shi, J. Zhou, P. Hong, B. Zhu, F. Hong, P. Qian, Q. Sun, X. Lu and L. Ye, Org. Chem. Front., 2022, 9, 2557 DOI: 10.1039/D2QO00123C

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