The use of butane diacetals of glycolic acid as precursors for the synthesis of the phytotoxic calmodulin inhibitor herbarumin II

被引：29

作者：

Díez, E ^{[1
]}

Dixon, DJ ^{[1
]}

Ley, SV ^{[1
]}

Polara, A ^{[1
]}

Rodríguez, F ^{[1
]}

机构：

[1] Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England

来源：

HELVETICA CHIMICA ACTA | 2003年 / 86卷 / 11期

关键词：

D O I：

10.1002/hlca.200390314

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The total synthesis of phytotoxic nonenolide herbarumin 11 (1) has been achieved by implementation of butane diacetal (BDA)-desymmetrised glycolate building blocks. Three of the four stereogenic centres present in the key coupling fragments were generated from both enantiomeric forms of the BDA building block in highly diastereoselective alkylation and aldol reactions.

引用

收藏

页码：3717 / 3729

页数：13

相关论文

共 52 条

[11]

2-D

[12]

Dixon DJ, 2002, SYNTHESIS-STUTTGART, P1973

[13] Highly diastereoselective lithium enolate aldol reactions of butane-2,3-diacetal desymmetrized glycolic acid and deprotection to enantiopure anti-2,3-dihydroxy esters [J].

Dixon, DJ ;

Ley, SV ;

Polara, A ;

Sheppard, T .

ORGANIC LETTERS, 2001, 3 (23) :3749-3752

[14] Highly diastereoselective Michael addition reactions of butane-2,3-diacetal desymmetrized glycolic acid.: Preparation of α-hydroxy-γ-amino acid derivatives [J].

Dixon, DJ ;

Ley, SV ;

Rodríguez, F .

ORGANIC LETTERS, 2001, 3 (23) :3753-3755

[15] The total synthesis of (+)-aspicilin using 2,3-butane diacetal protected butane tetrols via a chiral memory protocol [J].

Dixon, DJ ;

Foster, AC ;

Ley, SV .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 2001, 79 (11) :1668-1680

[16] A general and efficient procedure for the preparation of enantiopure anti-1,2-diols -: synthesis and utility of (R′,R′,S,R)-2,3-butane diacetal protected butane tetrol [J].

Dixon, DJ ;

Foster, AC ;

Ley, SV ;

Reynolds, DJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (12) :1635-1637

[17] Preparation of desymmetrised meso-tartrate derivatives -: synthesis and utility of (R′,R′,R,S)-2,3-butane diacetal protected dimethyl tartrate [J].

Dixon, DJ ;

Foster, AC ;

Ley, SV ;

Reynolds, DJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (12) :1631-1633

[18] Decanolides, 10-membered lactones of natural origin [J].

Drager, G ;

Kirschning, A ;

Thiericke, R ;

Zerlin, M .

NATURAL PRODUCT REPORTS, 1996, 13 (05) :365-375

[19] PINOLIDOXIN, A PHYTOTOXIC NONENOLIDE FROM ASCOCHYTA-PINODES [J].

EVIDENTE, A ;

LANZETTA, R ;

CAPASSO, R ;

VURRO, M ;

BOTTALICO, A .

PHYTOCHEMISTRY, 1993, 34 (04) :999-1003

[20] 3 NEW TOXIC PINOLIDOXINS FROM ASCOCHYTA-PINODES [J].

EVIDENTE, A ;

CAPASSO, R ;

ABOUZEID, MA ;

LANZETTA, R ;

VURRO, M ;

BOTTALICO, A .

JOURNAL OF NATURAL PRODUCTS, 1993, 56 (11) :1937-1943

← 1 2 3 4 5 6 →