659738-99-5

Upstream product

• 621-79-4 cinnamamide 
• 659739-06-7 Acetic acid (2R,4R,6S)-2-{(E)-(S)-2-(tert-butyl-dimethyl-silanyloxy)-5-[(E)-(3-phenyl-acryloyl)amino]-pent-4-enyl}-6-(2,2-dimethyl-4-oxo-4H-benzo[1,3]dioxin-5-ylmethyl)-tetrahydro-pyran-4-yl ester 

Relevant academic research and scientific papers

Total Synthesis and Biological Evaluation of (-)Apicularen A and Analogues Thereof

Apicularen A (1) and related benzolactone acylenamines belong to a growing class of novel natural products possessing highly cytotoxic properties. The challenging structure of 1 includes a 10-membered macrolactone ring, a tetrahydropyran system, an o,m-substituted phenol and a doubly unsaturated acyl group attached on the side chain enamine functionality. The total synthesis of apicularen A described herein involves a strategy equivalent to its proposed biosynthesis and entails a reiterative two-step procedure featuring allylation and ozonolytic cleavage to grow the molecule's chain by one acetate unit at a time. The developed synthetic technology was applied to the construction of a series of apicularen A analogues whose biological evaluation established a set of structure-activity relationships in this new area of potential importance in cancer chemotherapy.