887612-26-2Relevant 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
Enantioselective total synthesis of bistramide A
Crimmins, Michael T.,DeBaillie, Amy C.
, p. 4936 - 4937 (2007/10/03)
The enantioselective synthesis of bistramide A has been achieved with a longest linear sequence of 18 steps. The synthetic strategy involves the use of a distereoselective glycolate alkylation, an aldol addition of a chlorotitanium enolate of N-acylthiazolidinthione, and a Sharpless asymmetric epoxidation to synthesize the three key fragments. Copyright
