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Issue 20, 2018
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Construction of the tetracyclic core of (±)-cycloclavine and 4-amino Uhle's ketone

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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

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Publication details

The article was received on 11 Dec 2017, accepted on 23 Apr 2018 and first published on 09 May 2018


Article type: Paper
DOI: 10.1039/C7OB03067C
Citation: Org. Biomol. Chem., 2018,16, 3801-3808
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    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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