Acid Rearrangment of Epoxy-germacranolides and Absolute Configuration of 1β,10α-Epoxy-salonitenolide

6533b85dfe1ef96bd12be6fc

RESEARCH PRODUCT

Acid Rearrangment of Epoxy-germacranolides and Absolute Configuration of 1β,10α-Epoxy-salonitenolide

Kenneth F. Bastow Antonella Maggio Maurizio Bruno Kuo Hsiung Lee Sergio Rosselli Rosa Angela Raccuglia Susan L. Morris-natschke

subject

Pharmacology Natural product Stereochemistry Absolute configuration Salonitenolide Plant Science General Medicine Epoxy Acetonide Cnicin chemistry.chemical_compound Complementary and alternative medicine Breast cancer cell line chemistry visual_art Drug Discovery visual_art.visual_art_medium Organic chemistry Cytotoxicity

description

The acid-catalyzed cyclization of mono epoxides of cnicin acetonide (3) was investigated. Several 6,12-eudesmanolides were obtained, and their stereochemistry established by extensive spectroscopic analyses. Chemical correlations also led to the assignment of the absolute configuration of 1β,10α-epoxy-salonitenolide (13), a previously isolated natural product. The cytotoxic activities of some compounds were determined against A549 and MCF-7 tumor cell lines. The esterified germacranolides 2–6 were selectively cytotoxic against the MCF-7 breast cancer cell line.

year	journal	country	edition	language
2010-05-01	Natural Product Communications

https://doi.org/10.1177/1934578x1000500503

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