REARRANGEMENT OF ISOXAZOLINE-5-SPIRO DERIVATIVES .10. REGIOSELECTIVE NITRONE CYCLOADDITIONS TO METHOXYCARBONYLMETHYLENECYCLOPROPANE - SYNTHESIS OF PRECURSORS OF (PLUS-OR-MINUS)-LUPININE, (PLUS-OR-MINUS)-EPILUPININE AND (PLUS-OR-MINUS)-ELAEOKANINE-A

Citation
Fm. Cordero et al., REARRANGEMENT OF ISOXAZOLINE-5-SPIRO DERIVATIVES .10. REGIOSELECTIVE NITRONE CYCLOADDITIONS TO METHOXYCARBONYLMETHYLENECYCLOPROPANE - SYNTHESIS OF PRECURSORS OF (PLUS-OR-MINUS)-LUPININE, (PLUS-OR-MINUS)-EPILUPININE AND (PLUS-OR-MINUS)-ELAEOKANINE-A, Tetrahedron, 49(43), 1993, pp. 9867-9876
Citations number
26
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
ISSN journal
00404020
Volume
49
Issue
43
Year of publication
1993
Pages
9867 - 9876
Database
ISI
SICI code
0040-4020(1993)49:43<9867:ROID.R>2.0.ZU;2-Z
Abstract
The cycloaddition of cyclic nitrones to methoxycarbonylmethylenecyclop ropane (1) gives adducts having the methoxycarbonyl group on C4 of the isoxazolidine ring with high regioselectivity. The thermal rearrangem ent of the adducts gives quinolizidinone 6 and indolizidinones 8 beari ng the methoxycarbonyl group selectively at C-1 and at C-8, respective ly. The two compounds are intermediates for new formal syntheses of th e alkaloids (+/-)-Lupinine and (+/-)-Epilupinine, and (+/-)-Elaeokanin e A, respectively.