The formal divergent synthesis of natural products (-)-warburganal and synthesis of (+)-isodrimenin has been developed from α-hydroxy β,γ-unsaturated aldehyde I, which was easily prepared from available (+)-sclareolide in 5 steps. Reduction of intermediate I to II an aldehyde reduction provides a 10-step access to (-)-warburganal, while oxidation of I to III allylic oxidation and hemiacetalization facilitates a 9-step synthesis of (+)-isodrimenin.
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Formal synthesis of (-)-warburganal and synthesis of (+)-isodrimenin.
Nat Prod Res
March 2025
Weihai Marine Organism & Medical Technology Research Institute, Harbin Institute of Technology, Weihai, P. R. China.
The formal divergent synthesis of natural products (-)-warburganal and synthesis of (+)-isodrimenin has been developed from α-hydroxy β,γ-unsaturated aldehyde I, which was easily prepared from available (+)-sclareolide in 5 steps. Reduction of intermediate I to II an aldehyde reduction provides a 10-step access to (-)-warburganal, while oxidation of I to III allylic oxidation and hemiacetalization facilitates a 9-step synthesis of (+)-isodrimenin.
View Article and Find Full Text PDFStudy on the cytotoxic activity of drimane sesquiterpenes and nordrimane compounds against cancer cell lines.
Molecules
November 2014
Centro de Investigaciones Biomédicas (CIB), Escuela de Medicina, Universidad de Valparaíso, Av. Hontaneda N° 2664, Valparaíso 234000, Chile.
Twelve drimanes, including polygodial (1), isopolygodial (2), drimenol (3), confertifolin (4), and isodrimenin (5), were obtained from natural sources. Semi-synthetic derivatives 6-12 were obtained from 1 and 2, and cytotoxic activity was evaluated in vitro against cancer cell lines (HT-29, MDA-MB231, DHF, MCF-7, PC-3, DU-145, and CoN). IC50 values were determined at concentrations of 12.
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Phytochemistry
September 1999
Laboratoire de Chimie et Biochimie Pharmacologiques et Toxicologiques, UMR CNRS 8601, Université René Descartes-Paris V, France.
Incubation of confertifolin and isodrimenin with Mucor plumbeus, Aspergillus niger or Rhizopus arrhizus gave in good yields the corresponding 3 beta-hydroxy derivatives. From isodrimenin, the known natural 7 alpha-hydroxy derivative (futronolide) was also obtained and its structure was definitely established by X-ray crystallographic study of its acetate derivative.
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