ASYMMETRIC CONSTRUCTION OF ALPHA,ALPHA-DISUBSTITUTED CYCLOBUTANONES - ENANTIOSELECTIVE TOTAL SYNTHESIS OF (-)-FRONTALIN

被引：21
|
作者：
NEMOTO, H
YAMADA, T
ISHIBASHI, H
FUKUMOTO, K
机构：
来源：
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1991年 / 12期
关键词：
D O I：
10.1039/p19910003149
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Novel access to the chiral, alpha,alpha-disubstituted ketone 2-hydroxymethyl-2-methylcyclobutanone was developed, leading to an enantioselective total synthesis of (-)-frontalin, an aggregating pheromone of bark beetles.
引用
收藏
页码：3149 / 3151
页数：3
相关论文
共 50 条
  • [31] DESIGN AND SYNTHESIS OF CHIRAL CYCLIC ALPHA,ALPHA-DISUBSTITUTED ALPHA-AMINO ACIDS AND ITS PEPTIDES
    Demizu, Y.
    Tanaka, M.
    Anan, K.
    Yoshida, Y.
    Kurihara, M.
    Doi, M.
    Maruyama, T.
    Suemune, H.
    JOURNAL OF PEPTIDE SCIENCE, 2004, 10 : 125 - 125
  • [32] BENZOTRIAZOLE-MEDIATED SYNTHESIS OF ALPHA-DISUBSTITUTED AND ALPHA-TRISUBSTITUTED ETHERS AND SULFIDES
    KATRITZKY, AR
    JURCZYK, SC
    SZAJDA, M
    SHCHERBAKOVA, IV
    LAM, JN
    SYNTHESIS-STUTTGART, 1994, (05): : 499 - 504
  • [33] SYNTHESIS AND PHARMACOLOGICAL EVALUATION OF ALPHA,ALPHA-DISUBSTITUTED DERIVATIVES OF PHENYLACETAMIDE AND 1-NAPHTHYLACETAMIDE
    CASADIO, S
    PALA, G
    BRUZZESE, T
    CRESCENZI, E
    MARAZZIU.E
    COPPI, G
    JOURNAL OF MEDICINAL CHEMISTRY, 1965, 8 (05) : 594 - +
  • [34] SYNTHESIS AND PHARMACOLOGICAL EVALUATION OF ALPHA,ALPHA-DISUBSTITUTED DERIVATIVES OF PHENYLACETONITRILE AND 1-NAPHTHYLACETONITRILE
    CASADIO, S
    PALA, G
    CRESCENZI, E
    BRUZZESE, T
    MARAZZIU.E
    COPPI, G
    JOURNAL OF MEDICINAL CHEMISTRY, 1965, 8 (05) : 589 - +
  • [35] PREPARATION OF A NEW SERIES OF ALPHA,ALPHA-DISUBSTITUTED VINYL MONOMERS
    DEVARAJAN, R
    BALAKRISHNAN, T
    POLYMER BULLETIN, 1979, 1 (06) : 437 - 439
  • [36] PREPARATION OF KETONES FROM ALPHA,ALPHA-DISUBSTITUTED ACETOACETIC ESTERS
    RENFROW, WB
    WALKER, GB
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1948, 70 (11) : 3957 - 3958
  • [37] A NEW GENERAL-APPROACH TO ENANTIOMERICALLY PURE CYCLIC AND OPEN-CHAIN (R)-ALPHA,ALPHA-DISUBSTITUTED AND (S)-ALPHA,ALPHA-DISUBSTITUTED ALPHA-AMINO-ACIDS
    OBRECHT, D
    SPIEGLER, C
    SCHONHOLZER, P
    MULLER, K
    HEIMGARTNER, H
    STIERLI, F
    HELVETICA CHIMICA ACTA, 1992, 75 (05) : 1666 - 1696
  • [38] Enantioselective synthesis of alpha,alpha-disubstituted amino acid derivatives via enzymatic resolution: Preparation of a thiazolyl-substituted alpha-methyl alpha-benzyl amine
    Spero, DM
    Kapadia, SR
    JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (21): : 7398 - 7401
  • [39] ALPHA,ALPHA-DISUBSTITUTED ALLYL SULFONES - AN APPROACH TO THE SYNTHESIS OF VINYL-BRANCHED PHEROMONE ANALOGS
    HOSKOVEC, M
    KOUTEK, B
    LAZAR, J
    STREINZ, L
    BROZOVA, E
    KALINOVA, B
    VRKOC, J
    HELVETICA CHIMICA ACTA, 1994, 77 (05) : 1281 - 1287
  • [40] SYNTHESIS OF ALPHA,ALPHA-DISUBSTITUTED ALPHA-AMINO-ACID AMIDES BY PHASE-TRANSFER CATALYZED ALKYLATION
    KAPTEIN, B
    BOESTEN, WHJ
    BROXTERMAN, QB
    SCHOEMAKER, HE
    KAMPHUIS, J
    TETRAHEDRON LETTERS, 1992, 33 (40) : 6007 - 6010
12345