Stereoselective Transformations of (+)-Abietic Acid into (+)-Vitedoin B and (+)-Negundoin A

The first synthesis of spirolactone (+)-vitedoin B (14 steps, 8.0% global yield) and spiro enol ether (+)-negundoin A (19 steps, 3.7% global yield), via a nor-labdane acetoxy ester, has been achieved starting from commercial (+)-abietic acid.

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Bibliographic Details
Published in:Journal of organic chemistry 2014-05, Vol.79 (10), p.4405-4413
Main Authors: Tapia, Rubén, Bouanou, Hanane, Alvarez, Esteban, Alvarez-Manzaneda, Ramón, Chahboun, Rachid, Alvarez-Manzaneda, Enrique
Format: Article
Language:English
Subjects:
Cyclization
Diterpenes - chemical synthesis
Diterpenes - chemistry
Diterpenes, Abietane - chemistry
Molecular Structure
Spironolactone - analogs & derivatives
Spironolactone - chemical synthesis
Spironolactone - chemistry
Stereoisomerism
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Summary:The first synthesis of spirolactone (+)-vitedoin B (14 steps, 8.0% global yield) and spiro enol ether (+)-negundoin A (19 steps, 3.7% global yield), via a nor-labdane acetoxy ester, has been achieved starting from commercial (+)-abietic acid.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo5003533