REGIOSELECTIVITY OF 7-OXABICYCLO[2.2.1]HEPTA-2,5-DIENE-PHENOL REARRANGEMENT AS A FUNCTION OF THE ACID PROMOTER - STEREOSELECTIVE SYNTHESIS OF 1,2,3,4-TETRAHYDRO-2-HYDROXYNAPHTHALEN-2-YL METHYL KETONES

被引：15

作者：

ANTONSSON, T ^{[1
]}

VOGEL, P ^{[1
]}

机构：

[1] UNIV LAUSANNE,CHIM SECT,2 RUE BARRE,CH-1005 LAUSANNE,SWITZERLAND

来源：

TETRAHEDRON LETTERS | 1990年 / 31卷 / 01期

关键词：

D O I：

10.1016/S0040-4039(00)94341-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Successive Diels-Alder additions of 1-acetylvinyl p-nitrobenzoate and didehydrobenzene to 1-(dimethoxymethyl)-2,3,5,6-tetramethylidene-7-oxabicyclo[2.2.1] heptane led to 5-(dimethoxymethyl)-5,12-epoxy-2-(p-nitrobenzoyloxy)-l,2,3,4-tetrahydronaphthacen-2-yl methyl ketone with high regio- and stereoselectivity. The regioselectivity of the ethereal ring opening of the 7-oxanorbornadiene moiety of the latter compound depended on the Lewis acid promotor. © 1990.

引用

页码：89 / 92

页数：4

共 41 条

[1] NEW CYANOMORPHOLINYL BY-PRODUCT OF DOXORUBICIN REDUCTIVE ALKYLATION [J].

ACTON, EM ;

TONG, GL ;

TAYLOR, DL ;

FILPPI, JA ;

WOLGEMUTH, RL .

JOURNAL OF MEDICINAL CHEMISTRY, 1986, 29 (07) :1225-1230

[2] REGIOSELECTIVITY OF DIELS-ALDER ADDITIONS OF 1-ACETYLVINYL ARENECARBOXYLATES [J].

AGUILAR, R ;

REYES, A ;

TAMARIZ, J ;

BIRBAUM, JL .

TETRAHEDRON LETTERS, 1987, 28 (08) :865-868

[3] ADRIAMYCIN, 14-HYDROXYDAUNOMYCIN, A NEW ANTITUMOR ANTIBIOTIC FROM S-PEUCETIUS VAR CAESIUS [J].

ARCAMONE, F ;

CASSINEL.G ;

FANTINI, G ;

GREIN, A ;

OREZZI, P ;

POL, C ;

SPALLA, C .

BIOTECHNOLOGY AND BIOENGINEERING, 1969, 11 (06) :1101-&

[4]

ARCAMONE F, 1976, CANCER TREAT REP, V60, P829

[5] STRUCTURES OF NOVEL ANTHRACYCLINE ANTI-TUMOR ANTIBIOTICS FROM MICROMONOSPORA-PEUCETICA [J].

ARCAMONE, F ;

CASSINELLI, G ;

DIMATTEO, F ;

FORENZA, S ;

RIPAMONTI, MC ;

RIVOLA, G ;

VIGEVANI, A ;

CLARDY, J ;

MCCABE, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (04) :1462-1463

[6] ANTITUMOR ANTHRACYCLINES - RECENT DEVELOPMENTS [J].

ARCAMONE, F .

MEDICINAL RESEARCH REVIEWS, 1984, 4 (02) :153-188

[7]

ARCAMONE F, 1977, LLOYDIA, V40, P45

[8]

Arcamone F., 1981, DOXORUBICIN

[9]

BARBIERI B, 1984, DRUG EXP CLIN RES, V10, P85

[10] ANTHRACYCLINONES .2. SYNTHESIS OF (+/-)-4-DEMETHOXYDAUNOMYCINONE BY DOUBLE DIELS-ALDER ADDITIONS TO 2,3,5,6-TETRAMETHYLIDENE-7-OXANORBORNANE [J].

BESSIERE, Y ;

VOGEL, P .

HELVETICA CHIMICA ACTA, 1980, 63 (01) :232-243

← 1 2 3 4 5 →