SYNTHESIS OF ALPHA-TOCOPHEROL VIA 2-(SULFINYLMETHYL)CHROMANS

被引：9

作者：

AKKERMAN, JM ^{[1
]}

KONING, HD ^{[1
]}

HUISMAN, HO ^{[1
]}

机构：

[1] UNIV AMSTERDAM,ORGAN CHEM LAB,AMSTERDAM 1004,NETHERLANDS

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1979年 / 09期

关键词：

D O I：

10.1039/p19790002124

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2,5,7,8-Tetramethyl-2-[(phenylthio)methyl]chroman-6-ol, (6) was synthesized from trimethylhydroquinone (1) and 3-methyl-4-(phenylthio)buten-3-ol (12). Acetylation of (6) and subsequent oxidation gave 6-acetoxy-2,5,7,8-tetramethyl- 2-[(phenylsulphinyl)methyl]chroman (9). This was converted to the known α-tocopherol precursor 6-acetoxy-2,5,7,8-tetramethylchroman-2-carbaldehyde (4) by Pummerer reaction, hydrolysis, and reacetylation. An attempted more direct synthesis of α-tocopherol via alkylation of 6-(methoxymethoxy)-2,5, 7,8-tetramethyl-2-[(phenylsulphonyl)methyl]chroman (12) with hexahydrofarnesyl bromide led to ring opening and subsequent O-alkylation.

引用

页码：2124 / 2129

页数：6

共 21 条

[1]

AKKERMAN JM, UNPUBLISHED

[2]

AKKERMAN JM, THESIS

[3] BASE-CATALYZED DEUTERIUM EXCHANGE OF ACYCLIC SULFONES [J].

BROADDUS, CD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (20) :5504-&

[4] PHENYLTHIOMETHYLLITHIUM AND BIS(PHENYLTHIO)METHYLLITHIUM [J].

COREY, EJ ;

SEEBACH, D .

JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (12) :4097-&

[5] CARBON-SULFUR BOND-CLEAVAGE IN REACTION OF ALKYLLITHIUMS WITH SULFOXIDES [J].

DURST, T ;

LEBELLE, MJ ;

VANDENEL.R ;

TIN, KC .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1974, 52 (05) :761-766

[6] 2-STEP SYNTHESIS OF "(E)-4-CHLORO-2-METHYLCROTONALDEHYDE FROM ISOPRENE - UNPRECEDENTED OXIDATIVE CHLORINATION OF A 1,3-DIENE MONO-EPOXIDE BY CUPRIC CHLORIDE [J].

ELETTIBIANCHI, G ;

CENTINI, F ;

RE, L .

JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (09) :1648-1650

[7] THE PIONEER HISTORY OF VITAMIN-E [J].

EVANS, HM .

VITAMINS AND HORMONES, 1962, 20 :379-387

[8]

GEISS KH, 1974, ANGEW CHEM, V86, P484

[9] ORGANIC SYNTHESIS BY PUMMERER REACTION .1. SYNTHESIS OF ALPHA-HYDROXYALDEHYDES FROM BETA-HYDROXY SULFOXIDES [J].

IRIUCHIJIMA, S ;

MANIWA, K ;

TSUCHIHASHI, GI .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (13) :4280-4283

[10] GENERATION OF 3-CARBANION SPECIES FROM 3-PHENYLSULFINYL AND 3-PHENYLSULFONYL PROPIONIC ACIDS [J].

IWAI, K ;

KOSUGI, H ;

MIYAZAKI, A ;

UDA, H .

SYNTHETIC COMMUNICATIONS, 1976, 6 (05) :357-363

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