Total synthesis of apratoxin A.
[reaction: see text]. We have achieved a total synthesis of apratoxin A in which thiazoline formation was accomplished from the moCys containing amide 4 using PPh3(O)/Tf2O. Deprotection of the Troc and allyl ester in 17, coupling with tripeptide 3, and deprotection of the allyl ester and the Fmoc, followed by macrolactamization provided apratoxin A (1).
Doi
Takayuki
T
Department of Applied Chemistry, Tokyo Institute of Technology, 2-12-1, Ookayama, Meguro, Tokyo 152-8552, Japan. doit@apc.titech.ac.jp
Numajiri
Yoshitaka
Y
Munakata
Asami
A
Takahashi
Takashi
T
D000458:Cyanobacteria / Q000737:chemistry; D047630:Depsipeptides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013844:Thiazoles / Q000737:chemistry*
D047630:Depsipeptides; D013844:Thiazoles; C442201:apratoxin A