Synthesis 2020; 52(15): 2241-2244
DOI: 10.1055/s-0040-1708018
paper
© Georg Thieme Verlag Stuttgart · New York

BF3·OEt2-Catalyzed Aldol Condensation of Steroid Sapogenins and 2-Oxoacids: A Single Step Conversion of Steroid Spiroketals into Branched α,β-Unsaturated Spirolactones

Juan E. Hernández-Martínez
,
Facultad de Química, Universidad Nacional Autónoma de México, CDMX 04510, México   Email: martin.iglesias@unam.mx
› Author Affiliations
Financial support was provided by Dirección General de Asuntos del Personal Académico (Project DGAPA-IN218820), Consejo Nacional de Ciencia y Tecnología (Project A1-S-8019), and Facultad de Química, Universidad Nacional Autónoma de México (PAIP-5000-9063).
Further Information

Publication History

Received: 08 February 2020

Accepted after revision: 30 March 2020

Publication Date:
21 April 2020 (online)


Abstract

BF3·OEt2-catalyzed aldol reaction of steroid sapogenins with glyoxylic acid or pyruvic acid led to compounds in which the novel spirocyclic side chain bears an α,β-unsaturated lactone. The structures of the new spirolactones were established with the aid of combined 1D and 2D NMR techniques. A plausible mechanism is described.

Supporting Information

 
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