Total synthesis of the depsipeptide FR-901375.
The first total synthesis of FR-901375, a novel bicyclic depsipeptide isolated from the fermentation broth of Pseudomonas chloroaphis No. 2522, has been achieved. The synthetic approach involves 13 reaction steps and is achieved in 12% overall yield. The key points in the successful synthetic strategy are a concise asymmetric synthesis of the key building block (3R,4E)-3-hydroxy-7-mercapto-4-heptenoic acid, a mild Mitsunobu macrolactonization step, and an I(2)-mediated deprotection with concomitant disulfide-bridge formation.
Chen
Yanping
Y
Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA.
Gambs
Celine
C
Abe
Yoshito
Y
Wentworth
Paul
P
Janda
Kim D
KD
D047630:Depsipeptides; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D011549:Pseudomonas / Q000737:chemistry*
D047630:Depsipeptides; C482963:FR-901375; D010456:Peptides, Cyclic