Synthesis of aza bicyclic enones via anionic cyclization: application to the total synthesis of (-)-brunsvigine.
[reaction: see text] A general approach to the synthesis of aza bicyclic enones was developed via a simple two-step annulation involving a Mitsunobu protocol and anionic cyclization. According to this strategy the total synthesis of (-)-brunsvigine was accomplished with 12% overall yield.
Sha
C K
CK
Department of Chemistry, National Tsing Hua University, Hsinchu 300, Taiwan, ROC. cksha@mx.nthu.edu.tw
Hong
A W
AW
Huang
C M
CM
D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification*; D047151:Amaryllidaceae Alkaloids; D001372:Aza Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D018360:Crystallography, X-Ray; D003500:Cyclization; D015394:Molecular Structure; D010946:Plants, Medicinal / Q000737:chemistry*; D013329:Structure-Activity Relationship
D000470:Alkaloids; D047151:Amaryllidaceae Alkaloids; D001372:Aza Compounds; C432323:brunsvigine