Total synthesis of bistramide A and its 36(Z) isomers: differential effect on cell division, differentiation, and apoptosis
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Updated: May 22, 2026

Preclinical Assessment of the Bioactivity of the Anticancer Coumarin OT48 by Spheroids, Colony Formation Assays, and Zebrafish Xenografts
Published on: June 26, 2018
Loïc Tomas1, Gustav Boije af Gennäs, Marie Aude Hiebel
1Université de Lyon, ICBMS-UMR CNRS 5246, LCO2-Glycochimie, Université Claude Bernard Lyon 1, Bat. 308 CPE Lyon, 43, bd du 11 Novembre 1918, 69622 Villeurbanne Cedex, France.
Abstract:
The total synthesis of bistramide A and its 36(Z),39(S) and 36(Z),39(R) isomers shows that these compounds have different effects on cell division and apoptosis. The synthesis relies on a novel enol ether-forming reaction for the spiroketal fragment, a kinetic oxa-Michael cyclization reaction for the tetrahydropyran fragment, and an asymmetric crotonylation reaction for the amino acid fragment. Preliminary biological studies show a distinct pattern of influence of each of the three compounds on cell division, differentiation, and apoptosis in HL-60 cells, thus suggesting that these effects are independent activities of the natural product.
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