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Issue 22, 2014
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Synthesis of novel 1,2,3-triazolyl derivatives of pregnane, androstane and D-homoandrostane. Tandem “click” reaction/Cu-catalyzed D-homo rearrangement

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Abstract

Copper-catalyzed 1,3-dipolar cycloaddition has been employed in the reaction of steroidal azides with various terminal alkynes. A number of novel 1,2,3-triazolyl derivatives of pregnane, androstane and D-homoandrostane were obtained in high yield (70–98%). The developed synthetic protocols allowed us to attach the triazolyl moiety to both the side chain and the steroidal backbone directly, despite the steric hindrance exerted by the polycyclic system. The presence of Cu(II) was shown to evoke D-homo rearrangement under mild conditions. A rational choice of the copper precatalyst permitted us to carry out the “click” reaction either along with tandem D-homo rearrangement or in the absence of this process. The tendency of 16-heterosubstituted steroids to undergo D-homo rearrangement under Cu(II) catalysis was studied.

Graphical abstract: Synthesis of novel 1,2,3-triazolyl derivatives of pregnane, androstane and d-homoandrostane. Tandem “click” reaction/Cu-catalyzed d-homo rearrangement

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Publication details

The article was received on 21 Feb 2014, accepted on 02 Apr 2014 and first published on 04 Apr 2014


Article type: Paper
DOI: 10.1039/C4OB00404C
Citation: Org. Biomol. Chem., 2014,12, 3707-3720
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    Synthesis of novel 1,2,3-triazolyl derivatives of pregnane, androstane and D-homoandrostane. Tandem “click” reaction/Cu-catalyzed D-homo rearrangement

    Y. N. Kotovshchikov, G. V. Latyshev, N. V. Lukashev and I. P. Beletskaya, Org. Biomol. Chem., 2014, 12, 3707
    DOI: 10.1039/C4OB00404C

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