An efficient strategy for the synthesis of 5-hydroxyalkylbutan-4-olides from D-mannitol: total synthesis of (-)-muricatacin

被引：30

作者：

Chandrasekhar, M ^{[1
]}

Chandra, KL ^{[1
]}

Singh, VK ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, Kanpur 208016, Uttar Pradesh, India

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 15期

关键词：

D O I：

10.1016/S0040-4039(02)00375-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general approach towards the synthesis of 5-hydroxyalklbutan-4-olides front D-mannitol has been described. The approach has successfully been used for the total synthesis of (-)-muricatacin. an anti-tumor natural product. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：2773 / 2775

页数：3

共 35 条

[1] HIGHLY DIASTEREOSELECTIVE ALKYLATIONS OF CHIRAL AMIDE ENOLATES - NEW ROUTES TO HYDROXYETHYLENE DIPEPTIDE ISOSTERE INHIBITORS OF HIV-1 PROTEASE [J].

ASKIN, D ;

WALLACE, MA ;

VACCA, JP ;

REAMER, RA ;

VOLANTE, RP ;

SHINKAI, I .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (10) :2771-2773

[2] Total synthesis of asimicin and bullatacin [J].

Avedissian, H ;

Sinha, SC ;

Yazbak, A ;

Sinha, A ;

Neogi, P ;

Sinha, SC ;

Keinan, E .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (19) :6035-6051

[3] Study of the structure-activity relationships of the acetogenin of annonaceae, muricatacin and analogues [J].

Cave, A ;

Chaboche, C ;

Figadere, B ;

Harmange, JC ;

Laurens, A ;

Peyrat, JF ;

Pichon, M ;

Szlosek, M ;

CotteLafitte, J ;

Quero, AM .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1997, 32 (7-8) :617-623

[4] STEREOSELECTIVE SYNTHESIS OF N-BOC-O-BENZYL-(4S,5S)-5-AMINO-4-HYDROXY-6-PHENYLHEXANOIC ACID, THE HYDROXYETHYLENE ISOSTERIC MOIETY OF POTENT HIV-1 PROTEASE INHIBITOR [J].

CHAKRABORTY, TK ;

GANGAKHEDKAR, KK .

TETRAHEDRON LETTERS, 1991, 32 (16) :1897-1898

[5] Formal total synthesis of (+)-boronolide [J].

Chandrasekhar, M ;

Raina, S ;

Singh, VK .

TETRAHEDRON LETTERS, 2000, 41 (25) :4969-4971

[6] STEREOSPECIFIC SYNTHESIS OF (+)-MURICATACIN - A BIOLOGICALLY-ACTIVE ACETOGENIN DERIVATIVE [J].

FIGADERE, B ;

HARMANGE, JC ;

LAURENS, A ;

CAVE, A .

TETRAHEDRON LETTERS, 1991, 32 (51) :7539-7542

[7]

GANTE J, 1991, CHEM ZTG, V115, P215

[8] AN EFFICIENT SYNTHESIS OF HYDROXYETHYLENE DIPEPTIDE ISOSTERES - THE CORE UNIT OF POTENT HIV-1 PROTEASE INHIBITORS [J].

GHOSH, AK ;

MCKEE, SP ;

THOMPSON, WJ .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (23) :6500-6503

[9]

GRAFE U, 1982, J ANTIBIOT, V35, P609

[10]

Ha J.D., 1999, J AM CHEM SOC, V121, P10012, DOI DOI 10.1021/ja9925958

← 1 2 3 4 →