TERPENES IN ORGANIC-SYNTHESIS .14. SYNTHESIS OF S-(+)-HYDROPRENE FROM (+)-BETA-CITRONELLENE

被引：7

作者：

GAMALEVICH, GD

SEREBRYAKOV, EP

机构：

[1] N. D. Zelinskiy Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, 117913

来源：

RUSSIAN CHEMICAL BULLETIN | 1993年 / 42卷 / 02期

关键词：

TECHNICAL GRADE BETA-CITRONELLENE; S-2,6-DIMETHYL-7-OCTEN-3-ONE, WOLFF-KIZHNER REDUCTION; S-3,7-DIMETHYL-1-OCTANOL, ENANTIOMERIC ENRICHMENT;

D O I：

10.1007/BF00697081

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A seven-step synthesis of S-(+)-hydroprene (S-1) in similar to 20% overall yield starting from S-(+)-3,7-dimethyl-1,6-octadiene (2) of 55+/-10% optical purity is described. The introduction of an optical enhancement step in the synthetic sequence at the stage of S-(-)-3,7-dimethyl-1-octanol (9) raises the optical purity of S-1 from similar to 50% to similar to 80%.

引用

收藏

页码：300 / 306

页数：7

相关论文

共 11 条

[1] 3,7-DICARBETHOXY-5-HYDROXYTROPOLONE - A CONVENIENT SYNTHESIS OF PIMELIC ACID [J].

GARDNER, PD ;

RAND, L ;

HAYNES, GR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1956, 78 (14) :3425-3427

[2] INSECT JUVENILE HORMONE-ACTIVITY OF OPTICALLY-ACTIVE ALKYL (2E,4E)-3,7,11-TRIMETHYL-2,4-DODECADIENOATES AND OF ARYLTERPENOID ANALOGS [J].

HENRICK, CA ;

ANDERSON, RJ ;

STAAL, GB ;

LUDVIK, GF .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1978, 26 (03) :542-550

[3]

LOCK G, 1954, MONATSH, V85, P802

[4]

MAASALU A, 1983, EESTI NSV TEAD AKAD, V32, P170

[5] A STEREOCONTROLLED ACCESS TO (+/-)-PATCHOULI, (-)-PATCHOULI, AND (+)-PATCHOULI ALCOHOL [J].

NAF, F ;

DECORZANT, R ;

GIERSCH, W ;

OHLOFF, G .

HELVETICA CHIMICA ACTA, 1981, 64 (05) :1387-1397

[6] SYNTHESIS OF CHIRAL ALCOHOL AND ESTER PHEROMONES THROUGH ENZYME-CATALYZED HYDROLYSIS USING PSEUDOMONAS-FLUORESCENS LIPASE - PREPARATION OF (2R,6S,10S)-6,10-14-TRIMETHYLPENTADECAN-2-OL AND THE PROPIONATE OF (2R,8R)-8-METHYLDECAN-2-OL [J].

NAOSHIMA, Y ;

MUNAKATA, Y ;

YOSHIDA, S ;

FUNAI, A .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (03) :549-553

[7] ORGANOALUMINUM-PROMOTED CLAISEN REARRANGEMENT OF ALLYL VINYL ETHERS [J].

NONOSHITA, K ;

BANNO, H ;

MARUOKA, K ;

YAMAMOTO, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (01) :316-322

[8] SYNTHESIS OF S-(+)-HYDROPRENE [J].

ODINOKOV, VN ;

ISHMURATOV, GY ;

KHARISOV, RY ;

SEREBRYAKOV, EP ;

TOLSTIKOV, GA .

RUSSIAN CHEMICAL BULLETIN, 1993, 42 (01) :100-101

[9] OPTISCH AKTIVES BETA-CITRONELLOL AUS(+)-ODER(-)-PINAN [J].

RIENAECK.R ;

OHLOFF, G .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1961, 73 (07) :240-&

[10] CHIRAL BUILDING-BLOCKS BASED ON TECHNICAL GRADE BETA-CITRONELLENE [J].

SEREBRYAKOV, EP ;

HAO, NC ;

MAVROV, MV .

PURE AND APPLIED CHEMISTRY, 1990, 62 (10) :2041-2046