Total Synthesis of the Bridged Indole Alkaloid Apparicine

被引:57
作者
Bennasar, M. -Lluisa [1 ]
Zulaica, Ester
Sole, Daniel
Roca, Tomas
Garcia-Diaz, Davinia
Alonso, Sandra
机构
[1] Univ Barcelona, Fac Pharm, Organ Chem Lab, E-08028 Barcelona, Spain
关键词
RING-CLOSING METATHESIS; STEREOCONTROLLED SYNTHESIS; OLEFIN ISOMERIZATION; CONCISE SYNTHESIS; STRYCHNOS; CONSTRUCTION; ASPIDOSPERMA; CYCLOPROPANATION; AZEPINOINDOLE; BIOSYNTHESIS;
D O I
10.1021/jo901986v
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An indole-templated ring-closing metathesis or it 2-indolylacyl radical cyclization constitute the central steps of two alternative approaches developed to assemble the tricyclic ABC substructure of the indole alkaloid apparicine From this key intermediate, an intramolecular vinyl halide Heck reaction accomplished the closure of the strained 1-azabicyclo[4.2.2]decane framework of the alkaloid with concomitant incorporation of the exocyclic alkylidene substituents.
引用
收藏
页码:8359 / 8368
页数:10
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