Synthetic studies on the ingenane diterpenes. Construction of an ABC tricycle exhibiting trans-intrabridgehead stereochemistry

被引：21

作者：

Rigby, JH ^{[1
]}

Hu, JD ^{[1
]}

Heeg, MJ ^{[1
]}

机构：

[1] Wayne State Univ, Dept Chem, Detroit, MI 48202 USA

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 16期

关键词：

D O I：

10.1016/S0040-4039(98)00243-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Intramolecular, metal-promoted [6 pi+4 pi] cycloaddition followed by alkoxide accelerated 1,5-H sigmatropy affords a functionalized ingenane tricycle possessing the critical in,out-intrabridgehead stereochemical relationship. (C) 1998 Elsevier Science Ltd. All rights reserved.

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页码：2265 / 2268

页数：4

相关论文

共 22 条

[1]

Evans F.J., 1983, Pro-Inflammatory, Tumour-Promoting and Anti-Tumour Diterpenes of the Plant Families Euphorbiaceae and Thymelaeaceae, P1

[2] CYCLOHEPTATRIENE AND TROPYLIUM METAL-COMPLEXES .9. [1,5] HYDROGEN MIGRATIONS IN CYCLOHEPTATRIENES COMPLEXED TO CHROMIUM [J].

FOREMAN, MI ;

WATTS, WE ;

TODD, KH ;

PAUSON, PL ;

KNOX, GR .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1972, (09) :1141-&

[3] A SOLUTION TO THE IN,OUT-BICYCLO[4.4.1]UNDECAN-7-ONE PROBLEM INHERENT IN INGENANE TOTAL SYNTHESIS [J].

FUNK, RL ;

OLMSTEAD, TA ;

PARVEZ, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (10) :3298-3300

[4] STEREOSELECTIVE CONSTRUCTION OF THE COMPLETE INGENANE RING-SYSTEM [J].

FUNK, RL ;

OLMSTEAD, TA ;

PARVEZ, M ;

STALLMAN, JB .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (22) :5873-5875

[5] NEW TOXIC, IRRITANT AND COCARCINOGENIC DITERPENE ESTERS FROM EUPHORBIACEAE AND FROM THYMELAEACEAE [J].

HECKER, E .

PURE AND APPLIED CHEMISTRY, 1977, 49 (09) :1423-1431

[6]

HECKER E, 1982, CARCINOGENESIS, V7

[7] Approaches to the synthesis of ingenol [J].

Kim, S ;

Winkler, JD .

CHEMICAL SOCIETY REVIEWS, 1997, 26 (05) :387-399

[8] CYCLOHEPTATRIENE- AND TROPYLIUM-METAL COMPLEXES .1. NORMAL REACTION OF TRICARBONYLTROPYLIUMCHROMIUM SALTS WITH ANIONS [J].

MUNRO, JD ;

PAUSON, PL .

JOURNAL OF THE CHEMICAL SOCIETY, 1961, (AUG) :3475-&

[9] A new approach for ingenol synthesis [J].

Nakamura, T ;

Matsui, T ;

Tanino, K ;

Kuwajima, I .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (10) :3032-3033

[10] A STEREOCONTROLLED SYNTHETIC ENTRY TO THE PRIMARY PROSTAGLANDINS FROM BUTADIENE - OXY ANIONIC SUBSTITUENT EFFECTS ON [1,5]-HYDROGEN SIGMATROPY [J].

PAQUETTE, LA ;

CROUSE, GD ;

SHARMA, AK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (11) :3972-3974