Catalyst-controlled inverse-electron-demand hetero-Diels-Alder reactions in the enantio- and diastereloselective synthesis of iridoid natural products

被引：61

作者：

Chavez, DE ^{[1
]}

Jacobsen, EN ^{[1
]}

机构：

[1] Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 14期

关键词：

D O I：

10.1021/ol034883l

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHIC] Iridoid natural products 1-4 are accessed stereoselectively by means of tridentate (Schiff base)Cr(III)-catalyzed hetero-Diels-Alder reactions between ethyl vinyl ether and enantioenriched 5-methyl-1-cyclopentene-1-carboxaldehyde. An efficient route to the aldehyde from citronellal is afforded by the ring-closing metathesis reaction.

引用

页码：2563 / 2565

页数：3

共 30 条

[11]

2-2

[12]

Gademann K, 2002, ANGEW CHEM INT EDIT, V41, P3059, DOI 10.1002/1521-3773(20020816)41:16<3059::AID-ANIE3059>3.0.CO

[13]

2-I

[14] Catalytic asymmetric iodocarbocyclization reaction of 4-alkenylmalonates and its application to enantiotopic group selective reaction [J].

Inoue, T ;

Kitagawa, O ;

Saito, A ;

Taguchi, T .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (21) :7384-7389

[15] Catalyst-controlled diastereoselective hetero-Diels-Alder reactions [J].

Joly, GD ;

Jacobsen, EN .

ORGANIC LETTERS, 2002, 4 (10) :1795-1798

[16]

Kagan HB, 1996, CROAT CHEM ACTA, V69, P669

[17] SYNTHESE DES D,L-ISOIRIDOMYRMECINS [J].

KORTE, F ;

BUCHEL, KH ;

ZSCHOCKE, A .

CHEMISCHE BERICHTE-RECUEIL, 1961, 94 (08) :1952-1955

[18] Synthesis of cyclopenta[c]pyran skeleton of iridoid lactones [J].

Nangia, A ;

Prasuna, G ;

Rao, PB .

TETRAHEDRON, 1997, 53 (43) :14507-14545

[19] INTRAMOLECULAR HORNER-WADSWORTH-EMMONS REACTION IN BASE SENSITIVE SUBSTRATES - ENANTIOSPECIFIC SYNTHESIS OF IRIDOID MONOTERPENE LACTONES [J].

NANGIA, A ;

PRASUNA, G ;

RAO, PB .

TETRAHEDRON LETTERS, 1994, 35 (22) :3755-3758

[20]

Nicolaou KC, 2002, ANGEW CHEM INT EDIT, V41, P3276, DOI 10.1002/1521-3773(20020902)41:17<3276::AID-ANIE3276>3.0.CO

← 1 2 3 →