Studies toward the synthesis of (+)-palustrine: The first asymmetric synthesis of (-)-methyl palustramate

被引：30

作者：

Angle, SR ^{[1
]}

Henry, RM ^{[1
]}

机构：

[1] Univ Calif Riverside, Dept Chem, Riverside, CA 92521 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1998年 / 63卷 / 21期

关键词：

D O I：

10.1021/jo980749g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The stereoselective synthesis of(-)-methyl palustramate, a possible intermediate for the synthesis of(+)-palustrine, is described. The key step of the synthesis is a conformationally restricted Claisen rearrangement to afford the highly functionalized 1-benzylpipecolic ester 10. In addition, a new procedure for debenzylation of 1-benzylpiperidines (Li, (NH2CH2)(2), Et3N, THF) was used to remove the benzyl protecting group where traditional methods failed.

引用

页码：7490 / 7497

页数：8

共 31 条

[1] Synthesis of enantiopure indolizidine alkaloids from alpha-amino acids: Total synthesis of (-)-indolizidine 167B [J].

Angle, SR ;

Henry, RM .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (24) :8549-8552

[2] REDUCTION OF ORGANIC COMPOUNDS BY LITHIUM IN LOW MOLECULAR WEIGHT AMINES .1. SELECTIVE REDUCTION OF AROMATIC HYDROCARBONS TO MONOOLEFINS [J].

BENKESER, RA ;

ROBINSON, RE ;

SAUVE, DM ;

THOMAS, OH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1955, 77 (12) :3230-3233

[3] A NEW REDUCING SYSTEM - CALCIUM METAL IN AMINES - REDUCTION OF AROMATIC-HYDROCARBONS [J].

BENKESER, RA ;

BELMONTE, FG ;

KANG, J .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (17) :2796-2802

[4]

CARSON JF, 1981, SYNTHESIS-STUTTGART, P268

[5]

COREY EJ, 1979, TETRAHEDRON LETT, V5, P399

[6] ENANTIOSELECTIVE SYNTHESIS OF ALPHA-AMINO-ACID DERIVATIVES VIA THE STEREOSELECTIVE ALKYLATION OF A HOMOCHIRAL GLYCINE ENOLATE SYNTHON [J].

DELLARIA, JF ;

SANTARSIERO, BD .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (16) :3916-3926

[7]

EUGSTER CH, 1976, HETEROCYCLES, V4, P51

[8]

GARST ME, 1997, 213 NAT M AM CHEM SO

[9] Transition metal-mediated stereocontrolled cyclization of urethanes leading to versatile fused piperidines and its application to the synthesis of (+)-prosopinine and (+)-palustrine [J].

Hirai, Y ;

Watanabe, J ;

Nozaki, T ;

Yokoyama, H ;

Yamaguchi, S .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (04) :776-777

[10]

KAISER EM, 1972, SYNTH-INT J METHODS, P391

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