Efficient enantio- and diastereodivergent synthesis of poison-frog alkaloids 251O and trans-223B.
An efficient and flexible synthesis of poison-frog alkaloids 251O and trans-223B has been achieved by using for both alkaloids an enantiodivergent process starting from the common lactam 1. The relative stereochemistry of 251O and trans-223B was determined to be 7 (R = n-C(7)H(15), R' = n-Pr) and 14 by the present enantioselective synthesis.
Toyooka
Naoki
N
Graduate School of Medicine and Pharmaceutical Sciences, University of Toyama, Sugitani 2630, Toyama 930-0194, Japan. toyooka@pha.u-toyama.ac.jp
Zhou
Dejun
D
Nemoto
Hideo
H
Tezuka
Yasuhiro
Y
Kadota
Shigetoshi
S
Andriamaharavo
Nirina R
NR
Garraffo
H Martin
HM
Spande
Thomas F
TF
Daly
John W
JW
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000475:Alkenes / Q000737:chemistry; D000818:Animals; D002625:Chemistry, Organic / Q000379:methods*; D002849:Chromatography, Gas / Q000379:methods; D015195:Drug Design; D007700:Kinetics; D008956:Models, Chemical; D011042:Poisons / Q000737:chemistry; D011758:Pyrroles / Q000737:chemistry; D011763:Pyrrolizidine Alkaloids / Q000737:chemistry*; D011898:Ranidae; D017550:Spectroscopy, Fourier Transform Infrared / Q000379:methods; D013237:Stereoisomerism
D000470:Alkaloids; D000475:Alkenes; D011042:Poisons; D011758:Pyrroles; D011763:Pyrrolizidine Alkaloids; C545571:xenovenine