Synthesis of (4R)-Methylnonan-1-ol and (4R,8RS)-Dimethyldecanal from (S)-(+)-3,7-Dimethyl-1,6-octadiene

被引：0
|
作者：
G. Yu. Ismuratov
M. P. Yakovleva
A. V. Galyautdinova
G. A. Tolstikov
机构：
[1] Institute of Organic Chemistry,Russian Academy of Sciences
[2] Ufa Scientific Center,undefined
来源：
Chemistry of Natural Compounds | 2003年 / 39卷
关键词：
pheromone; (4R)-methylnonanol; (4R,8RS)-dimethyldecanal; (S)-(+)-dihydromyrcene; (6R,10)-dimethyl-9-yndecen-2-one; (6R)-methyl-9-hydroxynonan-2-one; sodium trisacetoxyborohydride; synthesis;
D O I：
暂无
中图分类号：
学科分类号：
摘要：
Optically active (4R,8RS)-dimethyldecanal, an analog of the aggregation pheromone of the flour beetles Tribolium confusum and T. Castaneum, and (4R)-methylnonan-1-ol, the sex pheromone of the yellow mealworm Tenebrio molitor L., are synthesized using ozonolytic transformation of (6R,10)-dimethyl-9-undecen-2-one to (6R)-methyl-9-hydroxynonan-2-one in the key step. The starting compound is available as enantiomerically enriched (ee ~50%) (S)-(+)-3,7-dimethyl-1,6-octadiene.
引用
收藏
页码：31 / 33
页数：2
相关论文
共 50 条
  • [21] Synthesis of terminal alkynes based on (1S,3R,4R)- and (1S,3S,4R)-2-azabicyclo[2.2.1]heptane
    Steppeler, Franz
    Gorecki, Marcin
    Wojaczynska, Elzbieta
    ARKIVOC, 2021, : 25 - 36
  • [22] NEW SYNTHESIS OF (4R,8R)-4,8-DIMETHYLDECANAL-PHEROMONE OF FLOUR BEETLES OF TRIBOILIUM-CONFUSUM AND T CASTANEUM
    KHAO, NK
    CHESKIS, BA
    MAVROV, MV
    MOISEENKOV, AM
    SEREBRYAKOV, EP
    ZHURNAL ORGANICHESKOI KHIMII, 1987, 23 (03): : 498 - 503
  • [23] PHEROMONES OF COLEOPTERA .7. SYNTHESIS OF (4R,8R)-4,8-DIMETHYLDECANAL, AGGREGATED PHEROMONE OF TRIBOLIUM (TENEBRIONDAE) BEETLES
    XAO, HK
    MAVROV, MV
    SEREBRYAKOV, EP
    ZHURNAL ORGANICHESKOI KHIMII, 1987, 23 (08): : 1649 - 1653
  • [24] ABSOLUTE-CONFIGURATION OF (-)-4-METHYLHEPTAN-3-OL, A PHEROMONE OF SMALLER EUROPEAN ELM BARK BEETLE, AS DETERMINED BY SYNTHESIS OF ITS (3R,4R)-(+)- AND (3S,4R)-(+)-ISOMERS
    MORI, K
    TETRAHEDRON, 1977, 33 (03) : 289 - 294
  • [25] An efficient synthesis of (3R,4R)-O-isopropylidene-1,6-hexanediol
    Saravanan, P
    Singh, VK
    SYNTHETIC COMMUNICATIONS, 2001, 31 (09) : 1383 - 1388
  • [26] An efficient stereoselective synthesis of (3S,4R)-4-(hydroxymethyl)pyrrolidin-3-ol from (S)-diethylmalate
    Kotian, PL
    Chand, P
    TETRAHEDRON LETTERS, 2005, 46 (19) : 3327 - 3330
  • [27] A concise, stereoselective and scalable synthesis of optically pure (3R,4R)-1-benzyl- and (3R,4R)-1-Boc-3-methyl-4-aminopiperidines
    Hazra, Sunit
    Kangune, Ankit
    Pawar, Govind
    Karmakar, Ananta
    Pabbisetty, Kumar B.
    Mortensen, Deborah S.
    Dodd, Dharmpal S.
    Li, Jianqing
    Mathur, Arvind
    Gupta, Anuradha
    Nimje, Roshan Y.
    TETRAHEDRON, 2024, 167
  • [28] TERPENYLATIONS USING (R)-(-)-ALPHA-PHELLANDRENE - SYNTHESIS OF THE (3S,4R)-8,9-DIHYDRO-ORTHO-CANNABIDIOL AND (3S,4R)-8,9-DIHYDRO-PARA-CANNABIDIOL, THEIR ISO-THCS, AND THE NATURAL DIHYDROCHALCONE (3S,4R)-(+)-LINDERATIN
    CROMBIE, L
    CROMBIE, WML
    FIRTH, DF
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (05): : 1251 - 1253
  • [29] SHORT SYNTHESIS OF (3S,4R)-3-HYDROXY-4-HYDROXYMETHYL-4-BUTANOLIDE AND (3R,4R)-3-HYDROXY-4-HYDROXYMETHYL-4-BUTANOLIDE, 2 LACTONES FROM LEVOGLUCOSENONE
    MATSUMOTO, K
    EBATA, T
    KOSEKI, K
    OKANO, K
    KAWAKAMI, H
    MATSUSHITA, H
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1995, 68 (02) : 670 - 672
  • [30] Syntheses of (3R,4R,5R,6R)-tetrahydroxyazepane (1,6-dideoxy-1,6-imino-D-mannitol) and (3S,4R,5R,6R)-tetrahydroxyazepane (1,6-dideoxy-1,6-imino-D-glucitol)
    Joseph, CC
    Regeling, H
    Zwanenburg, B
    Chittenden, GJF
    TETRAHEDRON, 2002, 58 (34) : 6907 - 6911
12345