Biomimetic Total Syntheses of (-)-TAN1251A, (+)-TAN1251B, (+)-TAN1251C, and (+)-TAN1251D

被引：35

作者：

Snider, BB ^{[1
]}

Lin, H ^{[1
]}

机构：

[1] Brandeis Univ, Dept Chem MS 015, Waltham, MA 02254 USA

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 05期

关键词：

D O I：

10.1021/ol991401q

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The muscarinic antagonists (-)-TAN1251A (1), (+)-TAN1251B (2), (+)-TAN1251C (3), and (+)-TAN1251D (4) have been synthesized biomimetically by enamine formation from an amino aldehyde to give TAN1251C ketal 18, Oxidation and reduction lead to TAN1251A (1), which has been hydroxylated to give TAN1251B (2), Stereospecific reduction of TAN1251C ketal 18 leads to TAN1251D (4).

引用

页码：643 / 646

页数：4

共 17 条

[1] ENANTIOSELECTIVE SYNTHESIS OF 7 PYRROLIZIDINE DIOLS FROM A SINGLE PRECURSOR [J].

CHAMBERLIN, AR ;

CHUNG, JYL .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (23) :4425-4431

[2]

CONAN JY, 1976, B SOC CHIM FR II-CH, P1935

[3] ASYMMETRIC HYDROXYLATION OF ENOLATES WITH N-SULFONYLOXAZIRIDINES [J].

DAVIS, FA ;

CHEN, BC .

CHEMICAL REVIEWS, 1992, 92 (05) :919-934

[4]

GRUNDKE G, 1987, SYNTHESIS-STUTTGART, P1115

[5]

HIDA T, 1999, COMMUNICATION 0506

[6] CONVENIENT MONOKETALIZATION OF 1,4-CYCLOHEXANEDIONE - SYNTHESIS OF NEW QUINONE METHIDES [J].

HYATT, JA .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (01) :129-131

[7]

Jones A. B., 1991, COMPREHENSIVE ORGANI, V7, P151

[8] A HIGHLY EFFICIENT AND GENERAL N-MONOMETHYLATION OF FUNCTIONALIZED PRIMARY AMINES VIA FORMYLATION BORANE METHYL SULFIDE REDUCTION [J].

KRISHNAMURTHY, S .

TETRAHEDRON LETTERS, 1982, 23 (33) :3315-3318

[9]

March J., 1992, ADV ORG CHEM, P357

[10] Total synthesis of (±)-TAN1251A [J].

Nagumo, S ;

Nishida, A ;

Yamazaki, C ;

Murashige, K ;

Kawahara, N .

TETRAHEDRON LETTERS, 1998, 39 (25) :4493-4496

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