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

被引：44

作者：

CORDERO, FM ^{[1
]}

ANICHINI, B ^{[1
]}

GOTI, A ^{[1
]}

BRANDI, A ^{[1
]}

机构：

[1] UNIV FLORENCE,CNR,CTR STUDIO CHIM & STRUTTURA COMPOSTI ETEROCICL & LORO APPLICAZ,I-50121 FLORENCE,ITALY

来源：

TETRAHEDRON | 1993年 / 49卷 / 43期

关键词：

D O I：

10.1016/S0040-4020(01)80188-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The cycloaddition of cyclic nitrones to methoxycarbonylmethylenecyclopropane (1) gives adducts having the methoxycarbonyl group on C4 of the isoxazolidine ring with high regioselectivity. The thermal rearrangement of the adducts gives quinolizidinone 6 and indolizidinones 8 bearing the methoxycarbonyl group selectively at C-1 and at C-8, respectively. The two compounds are intermediates for new formal syntheses of the alkaloids (+/-)-Lupinine and (+/-)-Epilupinine, and (+/-)-Elaeokanine A, respectively.

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页码：9867 / 9876

页数：10

相关论文

共 26 条

[1] LUPINEN-ALKALOIDE .8. ZUR KONFIGURATIONSBESTIMMUNG VON CHINOLIZIDIN-DERIVATEN [J].

BOHLMANN, F .

CHEMISCHE BERICHTE-RECUEIL, 1958, 91 (10) :2157-2167

[2] REARRANGEMENT OF ISOXAZOLINE-5-SPIRO DERIVATIVES .8. SELECTIVE FORMATION OF TETRAHYDROPYRIDONES FROM C,C-DISUBSTITUTED NITRONES [J].

BRANDI, A ;

DURUST, Y ;

CORDERO, FM ;

DESARLO, F .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (21) :5666-5670

[3]

BRANDI A, 1993, SYNLETT, P1

[4] REARRANGEMENT OF ISOXAZOLINE-5-SPIRO DERIVATIVES .2. SYNTHESIS AND REARRANGEMENT OF TETRAHYDROISOXAZOLE-5-SPIROCYCLOPROPANES - PREPARATION OF PRECURSORS OF QUINOLIZINE, ISOQUINOLINE, AND INDOLE ALKALOIDS [J].

BRANDI, A ;

GARRO, S ;

GUARNA, A ;

GOTI, A ;

CORDERO, F ;

DESARLO, F .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (11) :2430-2434

[5] THE REGIOSELECTIVITY OF NITRONE AND NITRILE OXIDE CYCLOADDITIONS TO ALKYLIDENECYCLOPROPANES [J].

BRANDI, A ;

CORDERO, FM ;

DESARLO, F ;

GANDOLFI, R ;

RASTELLI, A ;

BAGATTI, M .

TETRAHEDRON, 1992, 48 (16) :3323-3334

[6]

CHRISTL M, 1973, CHEM BER-RECL, V106, P3275, DOI 10.1002/cber.19731061016

[7] REARRANGEMENT OF ISOXAZOLINE-5-SPIRO DERIVATIVES .5. DIASTEREOFACIAL SELECTIVITY IN THE CYCLOADDITION OF SUBSTITUTED 5-MEMBERED CYCLIC NITRONES AND METHYLENECYCLOPROPANES - STEREOSELECTIVE SYNTHESIS OF 3,5-SUBSTITUTED INDOLIZIDINONES [J].

CORDERO, FM ;

BRANDI, A ;

QUERCI, C ;

GOTI, A ;

DESARLO, F ;

GUARNA, A .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (06) :1762-1767

[8]

DALY JW, 1986, ALKALOIDS CHEM BIOL, V4, P112

[9]

GANDOLFI R, COMMUNICATION

[10] MECHANISMS AND STEREOCHEMISTRY OF HETEROLYTIC FRAGMENTATION [J].

GROB, CA .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1969, 8 (08) :535-&