SYNTHESIS OF LENTIGINOSINE BY STEREOSELECTIVE CHIRAL NITRONE CYCLOADDITION AND THERMAL REARRANGEMENT OF STRAINED SPIROISOXAZOLIDINE

Authors
CORDERO FM CICCHI S GOTI A BRANDI A
Citation
Fm. Cordero et al., SYNTHESIS OF LENTIGINOSINE BY STEREOSELECTIVE CHIRAL NITRONE CYCLOADDITION AND THERMAL REARRANGEMENT OF STRAINED SPIROISOXAZOLIDINE, Tetrahedron letters, 35(6), 1994, pp. 949-952
Citations number
20
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
35
Issue
6
Year of publication
1994
Pages
949 - 952
Database
ISI
SICI code
0040-4039(1994)35:6<949:SOLBSC>2.0.ZU;2-A
Abstract
The total synthesis of Lentiginosine (3) is reported. The strategy is based on the 1,3-dipolar cycloaddition of a TBDPS protected 3,4-dihydr oxypyrroline N-oxide to methylenecyclopropane followed by the thermal rearrangement of the resulting spirocyclopropaneisoxazolidine to give the functionalised indolizidine skeleton. The compound shows an [alpha ](D) value identical, but opposite in sign, with that reported for the natural isomer which has been assigned the same absolute configuratio n.