A 5-MEMBERED ENANTIOPURE CYCLIC NITRONE FROM MALIC-ACID BY REGIOSELECTIVE OXIDATION OF CYCLIC HYDROXYLAMINE - SYNTHESIS OF (1S,7S,8AR)-OCTAHYDRO-1,7-DIHYDROXYINDOLIZINE

被引：127

作者：

CICCHI, S

GOTI, A

BRANDI, A

机构：

[1] UNIV FLORENCE,DIPARTIMENTO CHIM ORGAN U SCHIFF,I-50121 FLORENCE,ITALY

[2] UNIV FLORENCE,CNR,CTR COMPOSTI ETEROCICLICI,I-50121 FLORENCE,ITALY

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1995年 / 60卷 / 15期

关键词：

D O I：

10.1021/jo00120a016

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The chiral optically pure five-membered 3-tert-butoxy-1-pyrroline N-oxide (1) was synthesized by a convenient five-step procedure from diethyl L-malate. The key step is the regioselective HgO dehydrogenation of the N-hydroxypyrrolidine 6 obtained by double-nucleophilic displacement of a (bis)mesylate with hydroxylamine. A rationalization of the observed regioselectivity of the oxidation by studying the oxidation of a deuterated N-hydroxypyrrolidine 20 is reported. Nitrone 1 has been applied to the synthesis of a new (1S,7S,8aR)-1,7-dihydroxyindolizidine (28) via 1,3-dipolar cycloaddition strategies.

引用

页码：4743 / 4748

页数：6

共 33 条

[1] AZABICYCLIC ALCOHOLS .4. STEREOCHEMISTRY OF 1- AND 2-HYDROXYINDOLIZIDINE AND HYDROXYPYRROLIZIDINE SYSTEMS
AARON, HS
RADER, CP
WICKS, GE
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (11) : 3502 - &
[2] ALI SA, 1993, TETRAHEDRON LETT, V34, P5325
[3] PERACID INDUCED RING-OPENING OF ISOXAZOLIDINES - A MECHANISTIC STUDY
ALI, SA
WAZEER, MIM
[J]. TETRAHEDRON LETTERS, 1992, 33 (22) : 3219 - 3222
[4] ALI SA, 1994, J CHEM RES M, P301
[5] A NITRONE-BASED APPROACH TO THE ENANTIOSELECTIVE TOTAL SYNTHESIS OF (-)-ANISOMYCIN
BALLINI, R
MARCANTONI, E
PETRINI, M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (04) : 1316 - 1318
[6] REARRANGEMENT OF ISOXAZOLINE-5-SPIRO DERIVATIVES .8. SELECTIVE FORMATION OF TETRAHYDROPYRIDONES FROM C,C-DISUBSTITUTED NITRONES
BRANDI, A
DURUST, Y
CORDERO, FM
DESARLO, F
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (21) : 5666 - 5670
[7] A SHORT SYNTHESIS OF (+/-)-GEPHYROTOXIN 223AB
BRANDI, A
CORDERO, F
QUERCI, C
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (07) : 1748 - 1750
[8] BRANDI A, 1993, SYNLETT, P1
[9] THE REGIOSELECTIVITY OF NITRONE AND NITRILE OXIDE CYCLOADDITIONS TO ALKYLIDENECYCLOPROPANES
BRANDI, A
CORDERO, FM
DESARLO, F
GANDOLFI, R
RASTELLI, A
BAGATTI, M
[J]. TETRAHEDRON, 1992, 48 (16) : 3323 - 3334
[10] NITRONE CYCLOADDITIONS - SYNTHESIS OF (+/-)-ANDRACHAMINE
CARRUTHERS, W
COGGINS, P
WESTON, JB
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (08): : 2323 - 2327

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