BETA-KETOPHOSPHONATES - PRECURSORS OF LTB4 ANALOGS

被引：7

作者：

DURAND, T

SAVIGNAC, P

GIRARD, JP

ESCALE, R

ROSSI, JC

机构：

[1] UNIV MONTPELLIER 1,FAC PHARM,CNRS,CHIM MEDIATEURS & PHYSICOCHIM INTERACT BIOL LAB,F-34060 MONTPELLIER,FRANCE

[2] ECOLE POLYTECH,CHIM PHOSPHORE & METAUX TRANSIT LAB,F-91128 PALAISEAU,FRANCE

来源：

TETRAHEDRON LETTERS | 1990年 / 31卷 / 29期

关键词：

D O I：

10.1016/S0040-4039(00)97561-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The simultaneous addition to a suspension of HNa in THF at 50°C of β ketophosphonates, 5 or 6 (obtained by acylation of cupromethyl phosphonate 2) in the Horner-Wadsworth-Emmons reactions and saturated aldehydes provides good yields of α,β-unsaturated ketones. This has been applied successfully in the synthesis of keto- 12 leukotriene LTB3 12a. © 1990.

引用

收藏

页码：4131 / 4134

页数：4

相关论文

共 13 条

[1]

[Anonymous], 1977, WILEY ONLINE LIB

[2] HORNER-WADSWORTH-EMMONS REACTION - USE OF LITHIUM-CHLORIDE AND AN AMINE FOR BASE SENSITIVE COMPOUNDS [J].

BLANCHETTE, MA ;

CHOY, W ;

DAVIS, JT ;

ESSENFELD, AP ;

MASAMUNE, S ;

ROUSH, WR ;

SAKAI, T .

TETRAHEDRON LETTERS, 1984, 25 (21) :2183-2186

[3] REGIOCONTROLLED METALATION OF DIETHYL BETA-DIALKYLAMINOVINYLPHOSPHONATES - A NEW SYNTHESIS OF SUBSTITUTED BETA-KETOPHOSPHONATES [J].

BOECKMAN, RK ;

WALTERS, MA ;

KOYANO, H .

TETRAHEDRON LETTERS, 1989, 30 (36) :4787-4790

[4] LEUKOTRIENE-B - TOTAL SYNTHESIS AND ASSIGNMENT OF STEREOCHEMISTRY [J].

COREY, EJ ;

MARFAT, A ;

GOTO, G ;

BRION, F .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (27) :7984-7985

[5] SYNTHESIS OF THE 7-CIS ISOMER OF THE NATURAL LEUKOTRIENE-D4 [J].

ERNEST, I ;

MAIN, AJ ;

MENASSE, R .

TETRAHEDRON LETTERS, 1982, 23 (02) :167-170

[6] STEREOSPECIFIC SYNTHESIS OF LEUKOTRIENE B4 (LTB4) [J].

GUINDON, Y ;

ZAMBONI, R ;

LAU, CK ;

ROKACH, J .

TETRAHEDRON LETTERS, 1982, 23 (07) :739-742

[7] THE WITTIG OLEFINATION REACTION AND MODIFICATIONS INVOLVING PHOSPHORYL-STABILIZED CARBANIONS - STEREOCHEMISTRY, MECHANISM, AND SELECTED SYNTHETIC ASPECTS [J].

MARYANOFF, BE ;

REITZ, AB .

CHEMICAL REVIEWS, 1989, 89 (04) :863-927

[8] ALPHA-CUPROPHOSPHONATES .3. APPLICATION TO SYNTHESIS OF BETA-KETOPHOSPHONATES [J].

MATHEY, F ;

SAVIGNAC, P .

TETRAHEDRON, 1978, 34 (06) :649-654

[9] DIMETHYL (2-OXO-4-METHYL-3-PENTENYL)PHOSPHONATE AS A PRECURSOR OF ALPHA,ALPHA'-DIENONES - SHORT SYNTHESES OF (+/-)-ALPHA-ATLANTONE AND (+/-)-AR-TURMERONE [J].

MOTOYOSHIYA, J ;

MIYAJIMA, M ;

HIRAKAWA, K ;

KAKURAI, T .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (08) :1326-1327

[10]

NAKAMURA T, 1987, CHEM PHARM BULL, V35, P2635