Enantioselective synthesis of paraconic acids

被引：105

作者：

Chhor, RB ^{[1
]}

Nosse, B ^{[1
]}

Sörgel, S ^{[1
]}

Böhn, C ^{[1
]}

Seitz, M ^{[1
]}

Reiser, O ^{[1
]}

机构：

[1] Univ Regensburg, Inst Organ Chem, D-93053 Regensburg, Germany

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2003年 / 9卷 / 01期

关键词：

asymmetric synthesis; lactones; metathesis; natural products; total synthesis;

D O I：

10.1002/chem.200390019

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The development of a new method for the enantioselective synthesis of disubstituted gamma-butyrolactones is reported. Based on this strategy, the total synthesis of three paraconic acids, that is (-)-roccellaric acid, (-)-nephrosteranic acid and (-)protopraesorediosic acid, and the formal total synthesis of (-)-methylenolactocin and (-)-protolichesterinic acid is described, which are important because of their antibiotic and antitumor properties. Key steps of the synthesis are copper(I) -catalyzed asymmetric cyclopropanations of furans, highly diastereoselective Sakurai allylations, Lewis acid or Lewis base catalyzed retroaldol/lactonization cascades, and ruthenium(II)-catalyzed, intermolecular cross metathesis reactions.

引用

页码：260 / 270

页数：11

共 107 条

[1]

AHLBRECHT H, 1999, SYNTHESIS-STUTTGART, P356

[2]

Ariza X, 2001, SYNLETT, P120

[3] Asymmetric carbolithiation of 2-phenylselenofumarate derivatives: a short synthesis of (-)-roccellaric acid [J].

Bella, M ;

Margarita, R ;

Orlando, C ;

Orsini, M ;

Parlanti, L ;

Piancatelli, G .

TETRAHEDRON LETTERS, 2000, 41 (04) :561-565

[4]

Blandin V, 1999, EUR J ORG CHEM, V1999, P1787

[5] Enantioselective synthesis of (-)-roccellaric acid [J].

Böhm, C ;

Reiser, O .

ORGANIC LETTERS, 2001, 3 (09) :1315-1318

[6]

Böhm C, 2000, EUR J ORG CHEM, V2000, P2955

[7]

Braun M., 1992, ADV CARBANION CHEM, V1, P177

[8]

BRUCKNER C, 1988, J ORG CHEM, V53, P2440

[9]

Brummer O, 1997, CHEM-EUR J, V3, P441

[10] DIRECT METHODS FOR ALPHA-METHYLENE LACTONE SYNTHESIS USING ITACONIC ACID-DERIVATIVES [J].

CARLSON, RM ;

OYLER, AR .

JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (26) :4065-4069

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