A convenient and stereoselective synthesis of 11Z-3,4-Didehydroretinal by Horner-Emmons reaction using diphenyl phosphonate

被引：6

作者：

Wada, Akimori ^{[1
]}

Wang, Fei ^{[1
]}

Ito, Masayoshi ^{[1
]}

机构：

[1] Kobe Pharmaceut Univ, Dept Organ Chem Life Sci, Higashinada Ku, Kobe, Hyogo 6588558, Japan

来源：

CHEMICAL & PHARMACEUTICAL BULLETIN | 2008年 / 56卷 / 01期

关键词：

visual pigment; 11Z-3,4-didehydroretinal; diphenyl phosphonate; Horner - Emmons reaction; Z-selectivity;

D O I：

10.1248/cpb.56.112

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A convenient synthesis of 3,4-didehydroretinal was developed. The Horner - Emmons reaction between 3,4-didehydro-beta-ionone and diphenyl phosphonate in the presence of crown ether gave the retinonitrile as an isomeric mixture, in which the newly produced double bond was predominantly 11Z-form. After separation of the 11Z-form retinonitrile, it was converted into the corresponding retinal in good yield without isomerization of the double bonds.

引用

页码：112 / 114

页数：3

共 11 条

[1] EFFECT OF CATION AND TEMPERATURE ON HORNER-EMMONS REACTION - STEREOSELECTIVE SYNTHESIS OF Z OR E NITRILES
REDJAL, A
SEYDENPE.J
TETRAHEDRON LETTERS, 1974, (19) : 1733 - 1736
[2] PRACTICAL SYNTHESIS OF Z-UNSATURATED ESTERS BY USING A NEW HORNER-EMMONS REAGENT, ETHYL DIPHENYLPHOSPHONOACETATE
ANDO, K
TETRAHEDRON LETTERS, 1995, 36 (23) : 4105 - 4108
[3] Synthesis of an olefin-containing cyclic peptide using the solid-phase Horner-Emmons reaction
Bang, JK
Hasegawa, K
Kawakami, T
Aimoto, S
Akaji, K
TETRAHEDRON LETTERS, 2004, 45 (01) : 99 - 102
[4] Highly selective synthesis of Z-unsaturated esters by using new Horner-Emmons reagents, ethyl (diarylphosphono)acetates
Ando, K
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (07): : 1934 - 1939
[5] Stereoselective synthesis of tetrasubstituted (Z)-alkenes from aryl alkyl ketones utilizing the Horner-Wadsworth-Emmons reaction
Sano, S
Takehisa, T
Ogawa, S
Yokoyama, K
Nagao, Y
CHEMICAL & PHARMACEUTICAL BULLETIN, 2002, 50 (09) : 1300 - 1302
[6] SOLID-PHASE SYNTHESIS OF OLEFIN-CONTAINING HTLV-1 PROTEASE INHIBITORS USING HORNER-EMMONS REACTION
Akaji, K.
Bang, J. K.
Naka, H.
Kawakami, T.
Aimoto, S.
JOURNAL OF PEPTIDE SCIENCE, 2004, 10 : 203 - 203
[7] Solid-phase synthesis of olefin-containing HTLV-1 protease inhibitor using Horner-Emmons reaction
Akaji, Kenichi
Bang, Jeong Kyu
Naka, Hiromi
Kawakami, Toru
Aimoto, Saburo
Peptides 2004, Proceedings: BRIDGES BETWEEN DISCIPLINES, 2005, : 607 - 608
[8] Highly Z-selective synthesis of α,β-unsaturated nitriles using the Horner-Wadsworth-Emmons reaction
Ando, Kaori
Okumura, Miho
Nagaya, Shigeo
TETRAHEDRON LETTERS, 2013, 54 (15) : 2026 - 2028
[9] INTRAMOLECULAR MICHAEL-ADDITION-INDUCED Z-]E ISOMERIZATION OF HORNER-EMMONS REACTION-PRODUCTS DURING THE SYNTHESIS OF THE N(14)-C(18) SUBUNIT OF CYCLOTHEONAMIDE-A
ROTH, P
METTERNICH, R
TETRAHEDRON LETTERS, 1992, 33 (28) : 3993 - 3996
[10] Stereoselective synthesis of methyl (Z)-(4,4-difluoro-2,3,4,5-tetrahydro-1H-1-benzazepin-5-ylidene) acetate using a dianion Horner-Wadsworth-Emmons reagent
Shimada, Y
Akane, H
Taniguchi, N
Matsuhisa, A
Kawano, N
Tanaka, A
CHEMICAL & PHARMACEUTICAL BULLETIN, 2005, 53 (05) : 589 - 590

← 1 2 →