Issue 20, 2018

Construction of the tetracyclic core of (±)-cycloclavine and 4-amino Uhle's ketone

Abstract

A rapid construction of the tetracyclic core (±)-2 of (±)-cycloclavine (1) was accomplished in seven steps and 24% overall yield from commercially available aldehyde 7. Key features include a domino Friedel–Crafts/nitro-Michael reaction to construct the C ring and an intramolecular ammonolysis of a diester to close the D ring. In addition, a versatile 4-amino Uhle's ketone (±)-3 was afforded rapidly in five steps and 43% overall yield.

Graphical abstract: Construction of the tetracyclic core of (±)-cycloclavine and 4-amino Uhle's ketone

Supplementary files

Article information

Article type
Paper
Submitted
11 Dec 2017
Accepted
23 Apr 2018
First published
09 May 2018

Org. Biomol. Chem., 2018,16, 3801-3808

Construction of the tetracyclic core of (±)-cycloclavine and 4-amino Uhle's ketone

J. Chen, Y. Mi, Z. Shi and X. Cao, Org. Biomol. Chem., 2018, 16, 3801 DOI: 10.1039/C7OB03067C

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