Intramolecular Heck cyclization of α-sulfenyl enol triflates.: Asymmetric synthesis of a pentacyclic cardenolide precursor having functionality at C-11.

被引：35

作者：

Hynes, J ^{[1
]}

Overman, LE ^{[1
]}

Nasser, T ^{[1
]}

Rucker, PV ^{[1
]}

机构：

[1] Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 26期

基金：

美国国家卫生研究院;

关键词：

aldol reactions; Heck reactions; enantiospecificity; sterols; sulfones;

D O I：

10.1016/S0040-4039(98)00860-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A concise route to the core of complex cardenolides is described. The sequence features use of a sulfone to join enantioenriched A and D ring fragments and also control intramolecular aldolization to generate ring C and an intramolecular Heck cyclization of an alpha-sulfenyl enol triflate to form the steroid skeleton. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：4647 / 4650

页数：4

共 16 条

[1] PREPARATION OF BENZO[B]THIOPHENES BY PD(0)-CATALYZED INTRAMOLECULAR CYCLIZATION OF ALLYL (AND PROPARGYL) O-IODOPHENYL SULFIDES
ARNAU, N
MORENOMANAS, M
PLEIXATS, R
[J]. TETRAHEDRON, 1993, 49 (47) : 11019 - 11028
[2] A SHORT TOTAL SYNTHESIS OF ESTRONE DERIVATIVES - A NOVEL 1,3-REARRANGEMENT OF AN ALLYLIC NITRO-GROUP
BARLAAM, B
BOIVIN, J
ELKAIM, L
ELTONFARR, S
ZARD, SZ
[J]. TETRAHEDRON, 1995, 51 (06) : 1675 - 1684
[3] SYNTHESIS AND PHOTOCHEMICAL-REARRANGEMENT OF (1R,7AS)-1-(TERT-BUTYLDIPHENYLSILOXY)-7A-METHYL-5(7AH)-INDANONE
CAINE, D
KOTIAN, PL
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (24) : 6587 - 6593
[4] DANIEWSKI AR, 1986, B POLISH ACAD SCI, V32, P29
[5] A strategy for total synthesis of complex cardenolides
Deng, W
Jensen, MS
Overman, LE
Rucker, PV
Vionnet, JP
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (20) : 6760 - 6761
[6] INUBUSHI Y, 1974, CHEM PHARM BULL, V22, P349
[7] JENSEN MP, UNPUB
[8] LANTHANIDES IN ORGANIC-SYNTHESIS .2. REDUCTION OF ALPHA-HETEROSUBSTITUTED KETONES
MOLANDER, GA
HAHN, G
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (07) : 1135 - 1138
[9] HYDRATION OF UNSATURATED STEROIDS BY BROWN HYDROBORATION REACTION .I. MONOUNSATURATED STEROIDS
NUSSIM, M
MAZUR, Y
SONDHEIMER, F
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1964, 29 (05) : 1120 - &
[10] Enantioselective synthesis of cardenolide precursors using an intramolecular Heck reaction
Overman, LE
Rucker, PV
[J]. TETRAHEDRON LETTERS, 1998, 39 (26) : 4643 - 4646

← 1 2 →