Total synthesis of crambescidin 359.
[structure: see text] Crambescidin 359 (4), which is the "vessel part" of the pentacyclic guanidine alkaloid ptilomycalin A (1), was synthesized for the first time based upon successive 1,3-dipolar cycloaddition reaction. This synthesis established the absolute stereochemistry of 4.
Nagasawa
Kazuo
K
Institute of Molecular and Cellular Biosciences, The University of Tokyo, Yayoi, Bunkyo-ku, Tokyo 113-0032, Japan. nagasawa@iam.u-tokyo.ac.jp
Georgieva
Angelina
A
Koshino
Hiroyuki
H
Nakata
Tadashi
T
Kita
Tetsuya
T
Hashimoto
Yuichi
Y
D000470:Alkaloids / Q000138:chemical synthesis*; D000818:Animals; D002121:Calcium Channel Blockers / Q000138:chemical synthesis*; D019791:Guanidine; D006146:Guanidines; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D011161:Porifera / Q000737:chemistry; D013141:Spiro Compounds / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000470:Alkaloids; D002121:Calcium Channel Blockers; D006146:Guanidines; D013141:Spiro Compounds; C449038:crambescidin 359; C103200:ptilomycalin A; D019791:Guanidine