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Synthesis 2020; 52(15): 2241-2244
DOI: 10.1055/s-0040-1708018
DOI: 10.1055/s-0040-1708018
paper
BF3·OEt2-Catalyzed Aldol Condensation of Steroid Sapogenins and 2-Oxoacids: A Single Step Conversion of Steroid Spiroketals into Branched α,β-Unsaturated Spirolactones
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.
Key words
steroid sapogenins - glyoxylic acid - pyruvic acid - aldol condensation - spirolactone - NMRSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1708018.
- Supporting Information
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