Total synthesis of batzelladine D.
[structure: see text] Stereoselective total synthesis of batzelladine D was accomplished in 15 steps. This synthesis features (i) successive 1,3-dipolar cycloaddition reactions to form the 2,5-disubstituted pyrrolidine ring system, (ii) esterification of the side chain to the bicyclic guanidine carboxylate, a common synthetic intermediate of batzelladine alkaloids, and (iii) tricyclic guanidine formation under the Mitsunobu reaction conditions.
Ishiwata
Takanori
T
Institute of Molecular and Cellular Biosciences, The University of Tokyo, 1-1-1 Yayoi, Bunkyo-ku, Tokyo 113-0032, Japan.
Hino
Tomoyuki
T
Koshino
Hiroyuki
H
Hashimoto
Yuichi
Y
Nakata
Tadashi
T
Nagasawa
Kazuo
K
D000470:Alkaloids / Q000138:chemical synthesis*; D000818:Animals; D004951:Esterification; D019791:Guanidine / Q000138:chemical synthesis; D011161:Porifera / Q000737:chemistry; D011743:Pyrimidines / Q000138:chemical synthesis*; D011759:Pyrrolidines / Q000138:chemical synthesis; D013237:Stereoisomerism
D000470:Alkaloids; D011743:Pyrimidines; D011759:Pyrrolidines; C410707:batzelladine D; D019791:Guanidine; C032519:pyrrolidine