A new synthetic access to bicyclic polyhydroxylated alkaloid analogues from pyranosides.
A facile, versatile and stereoselective synthesis of bicyclic polyhydroxylated alkaloids as castanospermine analogues is described. The synthetic route started from methyl pyranosides. The key steps involved a high-yielding expeditious one-pot tandem reaction from alkenes to N-substituted delta-lactams. The delta-lactams were stereoselectively vinylated to give the dienes, which were followed by the ring-closing metathesis to produce the cyclized products. The functional group transformations of the resulting bicyclic compounds furnished diverse polyhydroxylated alkaloids in good yields.
Wang
Ning
N
State Key Laboratory of Natural and Biomimetic Drugs, Peking University, Xue Yuan Rd No. 38, Beijing 100191, China.
Zhang
Li-He
LH
Ye
Xin-Shan
XS
D000470:Alkaloids / Q000138:chemical synthesis / Q000737:chemistry*; D001643:Bridged Bicyclo Compounds / Q000737:chemistry*; D006027:Glycosides / Q000737:chemistry*; D006900:Hydroxylation; D011108:Polymers / Q000138:chemical synthesis* / Q000737:chemistry; D011714:Pyrans / Q000737:chemistry*; D013237:Stereoisomerism
D000470:Alkaloids; D001643:Bridged Bicyclo Compounds; D006027:Glycosides; D011108:Polymers; D011714:Pyrans