A flexible strategy based on a C2-symmetric pool of chiral substrates: concise synthesis of (+)-valienamine, key intermediate of (+)- pancratistatin, and conduramines A-1 and E.
A new strategy invoking a new application of the [3,3] sigmatropic rearrangement of allylic azides and the presence of a C(2) symmetry element within a pool of chiral substrates was evolved. Not only does this simple flexible strategy provide a concise approach to (+)-valienamine, but it also can readily be adopted for the synthesis of conduramines A-1 and E and the enantiopure azido carbonate 4, a key intermediate of (+)-pancratistatin.
Chang
Yuan-Kang
YK
Department of Chemistry, National Chung-Hsing University, Taichung 400, Taiwan, Republic of China.
Lo
Hong-Jay
HJ
Yan
Tu-Hsin
TH
D047151:Amaryllidaceae Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D003511:Cyclohexanols / Q000138:chemical synthesis* / Q000737:chemistry; D053138:Cyclohexenes / Q000138:chemical synthesis* / Q000737:chemistry; D003514:Cyclohexylamines / Q000138:chemical synthesis* / Q000737:chemistry; D006595:Hexosamines / Q000138:chemical synthesis* / Q000737:chemistry; D007546:Isoquinolines / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism
D047151:Amaryllidaceae Alkaloids; D003511:Cyclohexanols; D053138:Cyclohexenes; D003514:Cyclohexylamines; D006595:Hexosamines; D007546:Isoquinolines; C545152:conduramine A-1; C545151:conduramine E; C030791:valienamine; C044997:pancratistatin