861899-24-3Relevant articles and documents
Total synthesis of bistramide A and its 36(Z) isomers: Differential effect on cell division, differentiation, and apoptosis
Tomas, Loic,Boije Af Gennaes, Gustav,Hiebel, Marie Aude,Hampson, Peter,Gueyrard, David,Pelotier, Beatrice,Yli-Kauhaluoma, Jari,Piva, Olivier,Lord, Janet M.,Goekjian, Peter G.
, p. 7452 - 7466 (2012/07/28)
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. Copyright
Stereoselective synthesis of the C1-C13 fragment of bistramide A
Hiebel, Marie-Aude,Pelotier, Béatrice,Piva, Olivier
scheme or table, p. 5091 - 5093 (2011/01/12)
The C1-C13 fragment of bistramide A was prepared from 5-hexenoic acid in 15 linear steps and in 16% overall yield. The core 2,6-trans-tetrahydropyran ring was obtained via a kinetically controlled oxa- Michael cyclization from the corresponding chiral α,β
A short approach to the bicyclo[4.3.0]nonane fragment of stawamycin
Dias, Luiz C.,Melgar, Gliseida Z.,Jardim, Luciana S. A.
, p. 4427 - 4431 (2007/10/03)
The bicyclo[4.3.0]nonane (C11-C21) fragment of stawamycin has been prepared by a sequence involving 11 steps (10% overall yield) from methyl (R)-(-)-3-hydroxy-2-methylpropionate. Key steps are a Pd-catalysed Stille coupling reaction