334905-27-0Relevant articles and documents
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.
