SYNTHESIS OF (+ -)-SEPTICINE

Authors
YERXA BR YANG K MOORE HW
Citation
Br. Yerxa et al., SYNTHESIS OF (+ -)-SEPTICINE, Tetrahedron, 50(21), 1994, pp. 6173-6180
Citations number
22
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
50
Issue
21
Year of publication
1994
Pages
6173 - 6180
Database
ISI
SICI code
0040-4020(1994)50:21<6173:SO(->2.0.ZU;2-I
Abstract
The total synthesis of the indolizidine alkaloid, (+/-)-septicine (5) (27% overall yield) in 8 steps from dimethyl squarate is presented. Th e key step of the synthesis involves the ring expansion of s-(3,4-dime thoxyphenyl)-4-(1-pyrrolo)cyclobutenone 12 to the corresponding indoli zine-5,8-dione 6. The synthesis is highly convergent and thus could be used for the synthesis of a variety of analogs.