A CLAISEN REARRANGEMENT STRATEGY FOR THE 3-ATOM RING EXPANSION OF CYCLIC-KETONES - A TOTAL SYNTHESIS OF (+/-) PRECAPNELLADIENE

被引：41

作者：

PETASIS, NA

PATANE, MA

机构：

[1] Department of Chemistry, University of Southern California, Los Angeles

来源：

TETRAHEDRON LETTERS | 1990年 / 31卷 / 47期

关键词：

D O I：

10.1016/S0040-4039(00)97175-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The aldol products derived from cyclic ketone enolates undergo Baeyer-Villiger oxidation to give after dehydration the corresponding vinylic-substituted lactones. Titanium-mediated olefination followed by Claisen rearrangement leads to an overall three-atom ring-expansion. The application of this strategy to a concise total synthesis of (±) precapnelladiene (22) is reported. © 1990.

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页码：6799 / 6802

页数：4

相关论文

共 33 条

[1] TERPENOIDS .76. PRE-CAPNELLADIENE, A POSSIBLE BIOSYNTHETIC PRECURSOR OF THE CAPNELLANE SKELETON [J].

AYANOGLU, E ;

GEBREYESUS, T ;

BEECHAN, CM ;

DJERASSI, C .

TETRAHEDRON, 1979, 35 (09) :1035-1039

[2]

BIRCH AM, 1983, J C S PERKIN T 1, P913

[3] SYNTHETIC STUDIES DIRECTED TOWARD NATURALLY-OCCURRING CYCLOOCTANOIDS .1. TOTAL SYNTHESIS OF (+/-)-CEROPLASTOL-I [J].

BOECKMAN, RK ;

ARVANITIS, A ;

VOSS, ME .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (07) :2737-2739

[4] CONSTRUCTION OF LARGE CARBOCYCLIC RINGS BY IRELAND-CLAISEN REARRANGEMENT OF O-SILYLATED LACTONE ENOLATES - SYNTHESIS OF (+/-)-MUSCONE [J].

BRUNNER, RK ;

BORSCHBERG, HJ .

HELVETICA CHIMICA ACTA, 1983, 66 (08) :2608-2614

[5]

BUCHI G, 1970, J AM CHEM SOC, V92, P3126

[6] AN ENOLATE CLAISEN ROUTE TO C-PYRANOSIDES - DEVELOPMENT AND APPLICATION TO AN IONOPHORE SYNTHON [J].

BURKE, SD ;

ARMISTEAD, DM ;

SCHOENEN, FJ ;

FEVIG, JM .

TETRAHEDRON, 1986, 42 (11) :2787-2801

[7] THE DIOXANONE-TO-DIHYDROPYRAN CLAISEN REARRANGEMENT - SYNTHESIS OF C(7)-C(13) FRAGMENTS OF ERYTHRONOLIDE-A AND ERYTHRONOLIDE-B [J].

BURKE, SD ;

SCHOENEN, FJ ;

NAIR, MS .

TETRAHEDRON LETTERS, 1987, 28 (36) :4143-4146

[8] A NEW SYNTHESIS OF 8-MEMBERED LACTONES CONTAINING A 5,6-DOUBLE BOND [J].

CARLING, RW ;

HOLMES, AB .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (04) :325-326

[9] CLAISEN REARRANGEMENTS OF LACTONIC (SILYL) ENOLATES - A NEW ROUTE OF FUNCTIONALIZED CYCLOALKENES [J].

DANISHEFSKY, S ;

FUNK, RL ;

KERWIN, JF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (22) :6889-6891

[10] TOTAL SYNTHESES OF ML-236A AND COMPACTIN BY COMBINING THE LACTONIC (SILYL) ENOLATE REARRANGEMENT AND ALDEHYDE-DIENE CYCLOCONDENSATION TECHNOLOGIES [J].

DANISHEFSKY, SJ ;

SIMONEAU, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (07) :2599-2604

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