Asymmetric synthesis of 1-azaspiro[4.5]decanes via intramolecular dipolar cycloaddition of nitrones containing the bornane-10,2-sultam chiral auxiliary

被引：19

作者：

Bagley, MC ^{[1
]}

Oppolzer, W ^{[1
]}

机构：

[1] Univ Geneva, Dept Chim Organ, CH-1211 Geneva 4, Switzerland

来源：

TETRAHEDRON-ASYMMETRY | 2000年 / 11卷 / 12期

关键词：

D O I：

10.1016/S0957-4166(00)00205-6

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The intramolecular 1,3-dipolar cycloaddition of a cyclic nitrone, prepared by an asymmetric electrophilic enolate hydroxyamination using the (2R)-bornane-10,2-sultam chiral auxiliary, proceeds to give bridged and fused cycloadducts with total diastereocontrol. Reduction of the fused isoxazolidine provides a 1-azaspiro[4.5]-decane as a potential intermediate in the asymmetric synthesis of the cylindricine alkaloids. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：2625 / 2633

页数：9

共 32 条

[21] DIASTEREOSELECTIVE AND ENANTIOSELECTIVE SYNTHESES OF (-)-CONIINE, (-)-SOLENOPSIN-A, (-)-SOLENOPSIS-FUGAX VENOM AND (-)-XENOVENINE VIA DEOXYGENATIVE DECARBOXYLATION OF 2-CARBONYLSULTAM-SUBSTITUTED N-HYDROXY-PIPERIDINES AND N-HYDROXY-PYRROLIDINES [J].

OPPOLZER, W ;

BOCHET, CG ;

MERIFIELD, E .

TETRAHEDRON LETTERS, 1994, 35 (38) :7015-7018

[22] Synthesis of (-)-erythrodiene via intramolecular Pd-catalyzed Zn-ene reaction [J].

Oppolzer, W ;

Flachsmann, F .

TETRAHEDRON LETTERS, 1998, 39 (28) :5019-5022

[23] ASYMMETRIC-SYNTHESIS OF ALPHA-AMINO-ACIDS AND ALPHA-N-HYDROXYAMINO ACIDS FROM N-ACYLBORNANE-10,2-SULTAMS - 1-CHLORO-1-NITROSOCYCLOHEXANE AS A PRACTICAL [NH2+] EQUIVALENT [J].

OPPOLZER, W ;

TAMURA, O ;

DEERBERG, J .

HELVETICA CHIMICA ACTA, 1992, 75 (06) :1965-1978

[24] SYNTHESIS OF (-)-PINIDINE VIA ASYMMETRIC, ELECTROPHILIC ENOLATE HYDROXYAMINATION NITRONE REDUCTION [J].

OPPOLZER, W ;

MERIFIELD, E .

HELVETICA CHIMICA ACTA, 1993, 76 (02) :957-962

[25]

OPPOLZER W, UNPUB U GENEVE SWITZ

[26] Fasicularin, a novel tricyclic alkaloid from the ascidian Nephteis fasicularis with selective activity against a DNA repair-deficient organism [J].

Patil, AD ;

Freyer, AJ ;

Reichwein, R ;

Carte, B ;

Killmer, LB ;

Faucette, L ;

Johnson, RK ;

Faulkner, DJ .

TETRAHEDRON LETTERS, 1997, 38 (03) :363-364

[27] Synthetic studies on lepadiformine using the 2-azaallyl anion method [J].

Pearson, WH ;

Ren, Y .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (03) :688-689

[28] Synthetic studies on the perhydropyrrolo[2,1-j]quinoline marine alkaloids lepadiformine and cylindricine C using a 2-azapentadienyl anion cycloaddition. Synthesis of 2,13-diepilepadiformine (or 2-epi-11-deoxycylindricine C). [J].

Pearson, WH ;

Barta, NS ;

Kampf, JW .

TETRAHEDRON LETTERS, 1997, 38 (19) :3369-3372

[29] Synthesis of (+/-)-cylindricines A, D, and E [J].

Snider, BB ;

Liu, T .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (16) :5630-5633

[30]

STERZYCKI R, 1979, SYNTHESIS-STUTTGART, P724

← 1 2 3 4 →