Franzyk H, Frederiksen S M, Jensen S R
Department of Organic Chemistry, The Technical University of Denmark, Building 201, DK-2800, Lyngby, Denmark.
J Nat Prod. 2000 May;63(5):592-5. doi: 10.1021/np9905517.
The iridoid glucoside antirrhinoside (1) was transformed into polysubstituted 3-azabicyclo[3.3.0]octanes 3, 12, and 13 in 4 to 5 steps. Ozonolysis of the diacetonide of 1 and of its 7-deoxy-derivative 8 afforded cyclopentanoids 2 and 10, respectively. Conditions for the selective conversion of 2 and 10 into the corresponding ditosylates 4 and 11 were investigated. Cyclization of 4 and 11 was achieved with benzylamine and 2-methoxybenzylamine to yield bicyclic pyrrolidines 3, 12, and 13. Additional building blocks 14 and 15 were obtained by selective deprotection of the N-benzyl and isopropylidene moieties in 12 and 13, respectively.
环烯醚萜苷类化合物抗鼻苷（1）经4至5步反应转化为多取代的3 - 氮杂双环[3.3.0]辛烷3、12和13。1的二丙酮化物及其7 - 脱氧衍生物8经臭氧分解分别得到环戊烷类化合物2和10。研究了将2和10选择性转化为相应二对甲苯磺酸酯4和11的条件。用苄胺和2 - 甲氧基苄胺使4和11环化，得到双环吡咯烷3、12和13。分别通过选择性脱除12和13中的N - 苄基和异亚丙基部分获得了另外的结构单元14和15。
