THE SYNTHESIS OF (Z)-PENTA-2,4-DIEN-1-OL AND SUBSTITUTED (E)-PENTADIENOLS BY THE STEREOCHEMICALLY CONTROLLED HORNER-WITTIG REACTION

被引：15

作者：

BROWN, PS ^{[1
]}

GREEVES, N ^{[1
]}

MCELROY, AB ^{[1
]}

WARREN, S ^{[1
]}

机构：

[1] UNIV CAMBRIDGE,CHEM LAB,LENSFIELD RD,CAMBRIDGE CB2 1EW,ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1991年 / 06期

关键词：

D O I：

10.1039/p19910001485

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Acylation of Ph2P(O)Me with a lactone gives a Horner-Wittig intermediate with a Z-double bond protected as a Diels-Alder adduct with furan and hence (Z)-penta-2,4-dien-1-ol. Substituted (E)-penta-2,4-dien-1-ols are available by a more general route involving addition of enals to phosphine oxides, a regiochemically controlled allylic alcohol transposition, and a Horner-Wittig reaction. The geometry of only one double bond can be controlled.

引用

页码：1485 / 1492

页数：8

共 26 条

[1] TOTAL STEREOSELECTIVE SYNTHESIS OF ALPHA-ATLANTONE [J].

BABLER, JH ;

OLSEN, DO ;

ARNOLD, WH .

JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (12) :1656-1658

[2] FACILE METHOD FOR BIS-HOMOLOGATION OF KETONES TO ALPHA,BETA-UNSATURATED ALDEHYDES - APPLICATION TO SYNTHESIS OF CYCLOHEXANOID COMPONENTS OF BOLL-WEEVIL SEX ATTRACTANT [J].

BABLER, JH ;

COGHLAN, MJ .

SYNTHETIC COMMUNICATIONS, 1976, 6 (07) :469-474

[3] THE KINETICS OF ANIONOTROPIC REARRANGEMENT .8. MEDIUM COMPOSITION, ACIDITY FUNCTION, AND REACTION RATE [J].

BRAUDE, EA ;

STERN, ES .

JOURNAL OF THE CHEMICAL SOCIETY, 1948, (NOV) :1982-1984

[4] THE INTRAMOLECULAR DIELS-ALDER REACTION [J].

BRIEGER, G ;

BENNETT, JN .

CHEMICAL REVIEWS, 1980, 80 (01) :63-97

[5] TRANSPOSITION OF ALLYLIC ALCOHOLS CONTROLLED BY THE PH2PO GROUP - REAGENTS FOR ALPHA-HYDROXY-DIENE SYNTHESIS BY THE HORNER-WITTIG REACTION [J].

BROWN, PS ;

MCELROY, AB ;

WARREN, S .

TETRAHEDRON LETTERS, 1985, 26 (02) :249-252

[6] SYNTHESIS OF BUTENOLIDES FROM ALPHA-(PHENYLTHIO)-KETONES AND ALPHA-(PHENYTHIO)-ESTERS - CRYSTAL-STRUCTURE OF AN INTERMEDIATE BETA-PHENYLTHIO-GAMMA-LACTONE [J].

BROWNBRIDGE, P ;

EGERT, E ;

HUNT, PG ;

KENNARD, O ;

WARREN, S .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (10) :2751-2759

[7] APPLICATIONS OF THE STEREOCHEMICALLY-CONTROLLED HORNER-WITTIG REACTION - SYNTHESIS OF FENICULIN, (E)-NON-6-EN-1-OL, A PHEROMONE OF THE MEDITERRANEAN FRUIT-FLY, (E)-DEC-5-EN-1-OL, AND (Z)-DEC-5-EN-1-OL, TRI-SUBSTITUTED ALKENES, AND (Z)-ALPHA-BISABOLENE [J].

BUSS, AD ;

GREEVES, N ;

MASON, R ;

WARREN, S .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (12) :2569-2577

[8] THE STEREOCONTROLLED HORNER-WITTIG REACTION - SYNTHESIS OF DISUBSTITUTED ALKENES [J].

BUSS, AD ;

WARREN, S .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (11) :2307-2325

[9] SYNTHESIS OF SINGLE ISOMERS (E OR Z) OF UNSATURATED ALCOHOLS BY THE HORNER-WITTIG REACTION [J].

BUSS, AD ;

GREEVES, N ;

LEVIN, D ;

WALLACE, P ;

WARREN, S .

TETRAHEDRON LETTERS, 1984, 25 (03) :357-360

[10] DIRECT OXIDATION OF TERTIARY ALLYLIC ALCOHOLS - SIMPLE AND EFFECTIVE METHOD FOR ALKYLATIVE CARBONYL TRANSPOSITION [J].

DAUBEN, WG ;

MICHNO, DM .

JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (04) :682-685

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