Total synthesis of (-)- and (±)-frontalin via ring-closing metathesis

被引：59

作者：

Scholl, M ^{[1
]}

Grubbs, RH ^{[1
]}

机构：

[1] CALTECH, Div Chem & Chem Engn, Arnold & Mabel Beckman Labs Chem Synthesis, Pasadena, CA 91125 USA

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 08期

基金：

美国国家卫生研究院;

关键词：

D O I：

10.1016/S0040-4039(98)02677-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Racemic and enantiopure targets containing the 6,8-dioxabicyclo [3.2.1]octane skeleton, can be conveniently synthesized from monocyclic diene precursors using an intramolecular ruthenium-catalyzed ring-closing metathesis reaction as the key step. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：1425 / 1428

页数：4

共 16 条

[1]

Armstrong SK, 1998, J CHEM SOC PERK T 1, P371

[2] NEW LIGANDS AND IMPROVED ENANTIOSELECTIVITIES FOR THE ASYMMETRIC DIHYDROXYLATION OF OLEFINS [J].

BECKER, H ;

KING, SB ;

TANIGUCHI, M ;

VANHESSCHE, KPM ;

SHARPLESS, KB .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (13) :3940-3941

[3] ACROLEIN ACETALS AS ALLYL CATION PRECURSORS IN THE IONIC DIELS-ALDER REACTION [J].

GASSMAN, PG ;

SINGLETON, DA ;

WILWERDING, JJ ;

CHAVAN, SP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (07) :2182-2184

[4] Some recent applications of olefin metathesis in organic synthesis: A review [J].

Ivin, KJ .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1998, 133 (1-2) :1-16

[5]

Maezaki N, 1998, CHEM PHARM BULL, V46, P217

[6] Stereoselective synthesis of (+)-frontalin [J].

Majewski, M ;

Nowak, P .

TETRAHEDRON-ASYMMETRY, 1998, 9 (15) :2611-2617

[7]

Morehead A, 1998, CHEM COMMUN, P275

[8] SYNTHESIS OF OPTICALLY-ACTIVE FORMS OF FRONTALIN - PHEROMONE OF DENDROCTONUS BARK BEETLES [J].

MORI, K .

TETRAHEDRON, 1975, 31 (11-1) :1381-1384

[9]

Nishimura Y, 1998, EUR J ORG CHEM, V1998, P233

[10] Selective olefin metatheses - new tools for the organic chemist: A review [J].

Randall, ML ;

Snapper, ML .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1998, 133 (1-2) :29-40

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