334905-26-9Relevant academic research and scientific papers
Total syntheses of bengamides B and E
Kinder, Jr.,Wattanasin,Versace,Bair,Bontempo,Green,Lu,Marepalli,Phillips,Roche,Tran,Wang,Waykole,Xu,Zabludoff
, p. 2118 - 2122 (2007/10/03)
Total syntheses of the cytotoxic marine natural products bengamides B and E are described. Both bengamides are prepared via amide coupling of a protected polyhydroxylated lactone intermediate 9 with a suitably substituted aminocaprolactam intermediate. Lactone 9 is prepared in five steps from commercially available α-D-glucoheptonic γ-lactone. The key reactions are a selective deprotection of a 1,2-acetonide in the presence of a 1,3-acetonide and an (E)-selective olefination of an unstable aldehyde using a gem-dichromium reagent. The bengamide B lactam intermediate 10 is prepared in seven steps from commercially available (5R)-5-hydroxy-L-lysine (12). The desired S-configuration at the γ-OH lactam position is established using the Mitsunobu reaction.
Synthesis and antitumor activity of ester-modified analogues of bengamide B
Kinder Jr.,Versace,Bair,Bontempo,Cesarz,Chen,Crews,Czuchta,Jagoe,Mou,Nemzek,Phillips,Tran,Wang,Weltchek,Zabludoff
, p. 3692 - 3699 (2007/10/03)
Bengamide B, a novel sponge-derived marine natural product with broad spectrum antitumor activity, was not suitable for further preclinical development because of its difficult synthesis and very poor water solubility. Bengamide B produced a 31% T/C at it
