Synthesis of (4S,6S)-4-hydroxy-1,7-dioxaspiro[5.5]undecane, a component of the olive fruit fly pheromone, by employing a novel asymmetric oxy-Michael addition

被引：0

作者：

Watanabe, H ^{[1
]}

Itoh, D ^{[1
]}

Kitahara, T ^{[1
]}

机构：

[1] Univ Tokyo, Dept Appl Biol Chem, Bunkyo Ku, Tokyo 1138657, Japan

来源：

SYNTHESIS-STUTTGART | 2000年 / 13期

关键词：

pheromone; olive fruit fly; Bactrocera oleae; oxy-Michael addition; asymmetric reaction; Wittig reactions; stereoselective synthesis; protecting groups;

D O I：

暂无

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The pheromone component 3 of the olive fruit fly was synthesized in an optically pure form. The key step of the synthesis is a novel asymmetric oxy-Michael addition, which was recently developed by our group.

引用

页码：1925 / 1929

页数：5

共 26 条

[1] IDENTIFICATION AND SYNTHESIS OF THE MAJOR SEX-PHEROMONE OF THE OLIVE FLY (DACUS-OLEAE) [J].

BAKER, R ;

HERBERT, R ;

HOWSE, PE ;

JONES, OT ;

FRANCKE, W ;

REITH, W .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1980, (02) :52-53

[2] ISOLATION AND SYNTHESIS OF 3-HYDROXY-1 AND 4-HYDROXY-1,7-DIOXASPIRO[5.5]UNDECANES FROM THE OLIVE FLY (DACUS-OLEAE) [J].

BAKER, R ;

HERBERT, RH ;

PARTON, AH .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1982, (11) :601-603

[3] [2+3] CYCLOADDITIONS OF ENANTIOMERICALLY PURE OXAZOLINE N-OXIDES - AN ALTERNATIVE TO THE ASYMMETRIC ALDOL CONDENSATION [J].

BERRANGER, T ;

LANGLOIS, Y .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (06) :1720-1726

[4] ENANTIOSPECIFIC SYNTHESIS OF (3S,6R)-3-HYDROXY-1,7-DIOXASPIRO[5.5]UNDECANE AND ITS (4R)-4-HYDROXY ISOMER [MINOR COMPONENTS OF OLIVE FRUIT-FLY (DACUS-OLEAE) SEX-PHEROMONE [J].

CUBERO, II ;

LOPEZESPINOSA, MTP ;

CASTILLO, RA .

JOURNAL OF CHEMICAL ECOLOGY, 1992, 18 (02) :115-125

[5] NUCLEAR MAGNETIC-RESONANCE ENANTIOMER REAGENTS - CONFIGURATIONAL CORRELATIONS VIA NUCLEAR MAGNETIC-RESONANCE CHEMICAL-SHIFTS OF DIASTEREOMERIC MANDELATE, O-METHYLMANDELATE, AND ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETATE (MTPA) ESTERS [J].

DALE, JA ;

MOSHER, HS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (02) :512-519

[6] DIASTEREOSELECTIVE SYNTHESIS OF PROTECTED SYN 1,3-DIOLS BY BASE-CATALYZED INTRAMOLECULAR CONJUGATE ADDITION OF HEMIACETAL-DERIVED ALKOXIDE NUCLEOPHILES [J].

EVANS, DA ;

GAUCHETPRUNET, JA .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (09) :2446-2453

[7] Enantioselective synthesis of altohyrtin C (spongistatin 2): Synthesis of the AB- and CD-spiroketal subunits [J].

Evans, DA ;

Coleman, PJ ;

Dias, LC .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1997, 36 (24) :2738-2741

[8] SEX-SPECIFIC ACTIVITY OF "(R)-(-)-1,7-DIOXASPIRO[5.5]UNDECANE (S)-(+)-1,7-DIOXASPIRO[5.5]UNDECANE, THE MAJOR PHEROMONE OF DACUS-OLEAE (DIPTERA, TEPHRITIDAE) [J].

HANIOTAKIS, G ;

FRANCKE, W ;

MORI, K ;

REDLICH, H ;

SCHURIG, V .

JOURNAL OF CHEMICAL ECOLOGY, 1986, 12 (06) :1559-1568

[9] MOLECULAR SIEVE-ASSISTED OXIDATIONS - NEW METHODS FOR CARBOHYDRATE DERIVATIVE OXIDATIONS [J].

HERSCOVICI, J ;

ANTONAKIS, K .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1980, (12) :561-562

[10] MILBEMYCIN SYNTHESIS - ASYMMETRIC-SYNTHESIS OF SPIROKETALS FROM METHYL ALPHA-D-GLUCOPYRANOSIDE [J].

KHANDEKAR, G ;

ROBINSON, GC ;

STACEY, NA ;

THOMAS, EJ ;

VATHER, S .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (13) :1507-1519

← 1 2 3 →