Reinvestigation of palladium-catalyzed allylation of the monoacetate of 4-cyclopentene-1,3-diol and synthesis of the coronafacic acid ethyl ester

被引：1

作者：

Kinouchi, Wataru ^{[1
]}

Kosaki, Yusuke ^{[1
]}

Kobayashi, Yuichi ^{[1
]}

机构：

[1] Tokyo Inst Technol, Dept Bioengn, Midori Ku, Yokohama, Kanagawa 2268501, Japan

来源：

TETRAHEDRON LETTERS | 2013年 / 54卷 / 51期

关键词：

Palladium; Allylic substitution; 4-Cyclopentene-1,3-diol monoacetate; beta-Keto ester; Coronafacic acid; ASYMMETRIC TOTAL SYNTHESES; (+)-CORONAFACIC ACID; BUILDING-BLOCKS; ALKYLATION; STEREOCHEMISTRY; CONFIGURATION; JASMONATE; QUININE;

D O I：

10.1016/j.tetlet.2013.10.052

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A larger quantity of a beta-keto ester that is 1.5-1.7 equiv more than the base (t-BuOK, NaH) was found to be essential in securing sufficient yields of the products in the palladium-catalyzed allylic substitution of the monoacetate of 4-cyclopentene-1,3-diol with beta-keto esters. This requirement also works well for substitutions with the TBS ether of the monoacetate and the monoacetate of 2-cyclohexene-1,4-diol. As an application, the coronafacic acid ethyl ester was synthesized as an optically active form. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：7017 / 7020

页数：4

共 36 条

[1] Highly efficient total synthesis of Δ12-PGJ2, 15-deoxy-Δ12,14-PGJ2, and their analogues
Acharya, HP
Kobayashi, Y
[J]. TETRAHEDRON, 2006, 62 (14) : 3329 - 3343
[2] Total synthesis of 2-(5,6-epoxyisoprostane A2)phosphorylcholine and elucidation of the relative configuration of the isoprostane moiety
Acharya, HP
Kobayashi, Y
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (22) : 3481 - 3484
[3] Regioselective catalytic asymmetric reaction of Horner-Wadsworth-Emmons reagents with enones: The odyssey of chiral aluminum catalysts
Arai, T
Sasai, H
Yamaguchi, K
Shibasaki, M
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (02) : 441 - 442
[4] BACKVALL JE, 1984, J ORG CHEM, V49, P4619
[5] RESEARCH ON SERIES OF CYCLITOLS .38. CONFORMATIONAL STUDIES OF 3,5-DISUBSTITUTED CYCLOPENTENE DERIVATIVES
COCU, FG
[J]. HELVETICA CHIMICA ACTA, 1970, 53 (04) : 739 - &
[6] Deardorff D. R., 1998, ORG SYNTH, V6, P487
[7] ENANTIOSELECTIVE PREPARATION OF FUNCTIONALIZED CYCLOPENTANOIDS VIA A COMMON CHIRAL (PI-ALLYL)PALLADIUM COMPLEX
DEARDORFF, DR
LINDE, RG
MARTIN, AM
SHULMAN, MJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (11) : 2759 - 2762
[8] STRUCTURE OF CORONATINE
ICHIHARA, A
SHIRAISHI, K
SATO, H
SAKAMURA, S
NISHIYAMA, K
SAKAI, R
FURUSAKI, A
MATSUMOTO, T
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (02) : 636 - 637
[9] ICHIHARA A, 1979, TETRAHEDRON LETT, P365
[10] Improved synthesis of quinine alkaloids with the Teoc protective group
Igarashi, J
Kobayashi, Y
[J]. TETRAHEDRON LETTERS, 2005, 46 (37) : 6381 - 6384

← 1 2 3 4 →