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
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
  • [31] Synthesis of (1S,4R)-4-isopropyl-1-methyl-2-cyclohexen-1-ol, the aggregation pheromone of the ambrosia beetle Platypus quercivorus, its racemate, (1R,4R)- and (1S,4S)-isomers
    Mori, Kenji
    TETRAHEDRON-ASYMMETRY, 2006, 17 (14) : 2133 - 2142
  • [32] Synthesis of (+)-(1R,2R,4R,6S)-1,6-epoxy-4-benzyloxycyclohexan-2-ol, a key precursor to inositol monophosphatase inhibitors, from (-)-quinic acid
    Schulz, J
    Beaton, MW
    Gani, D
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (06): : 943 - 954
  • [33] (3S,4R)-4-(2,5-dimethoxyphenyl)-8-methoxy-isochroman-3-ol
    Palusiak, M
    Malecka, M
    Grabowski, SJ
    Epsztajn, J
    Bieniek, A
    Kowalska, JA
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2002, 58 : O620 - O622
  • [34] STRUCTURE DU N,N-DIMETHYL-CAMPHRECARBOTHIOAMIDE-3 (1R,3S,4R)
    ROQUES, R
    LAMAZOUERE, AM
    SOTIROPOULOS, J
    DECLERCQ, JP
    GERMAIN, G
    ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE, 1980, 36 (JUL): : 1569 - 1572
  • [35] Synthesis of (4R)- and (4S)-[4-2H1] Geraniol
    Lee, D. H.
    Song, H. A.
    Shin, E. H.
    Lee, E. J.
    Kim, Y. Y.
    Jung, D. I.
    Hahn, J. T.
    ASIAN JOURNAL OF CHEMISTRY, 2011, 23 (11) : 4973 - 4976
  • [36] Synthesis of (-)-(1R,2R,4R,6S)-1,6-epoxy-4-benzyloxycyclohexan-2-ol, a key precursor to inositol monophosphatase inhibitors, from (-)-quinic acid.
    Schulz, J
    Gani, D
    TETRAHEDRON LETTERS, 1997, 38 (01) : 111 - 114
  • [37] Synthesis of (2S,3R,4R)-Dihydroxyisoleucine for Use in Amatoxin Synthesis
    Chandra, Shambhu Deo
    Gunasekera, Shanal
    Noichl, Benjamin Philipp
    Patrick, Brian O.
    Perrin, David M.
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (17): : 12739 - 12747
  • [38] Chemoenzymatic synthesis of (3R,4S)- and (3S,4R)-3-methoxy-4-methylaminopyrrolidine
    Kamal, Ahmed
    Shaik, Ahmad Ali
    Sandbhor, Mahendra
    Malik, M. Shaheer
    Azeeza, Shaik
    TETRAHEDRON-ASYMMETRY, 2006, 17 (20) : 2876 - 2883
  • [39] Chemoenzymatic synthesis of (3S,4S)- and (3R,4R)-3-methoxy-4-methylaminopyrrolidine
    Kamal, A
    Shaik, AA
    Sandbhor, M
    Malik, MS
    Kaga, H
    TETRAHEDRON LETTERS, 2004, 45 (43) : 8057 - 8059
  • [40] Asymmetric synthesis of (2S,3R,4R)-ethoxycarbonylcyclopropyl phosphonoglycine
    Hannour, S
    Roumestant, ML
    Viallefont, P
    Riche, C
    Martinez, J
    El Hallaoui, A
    Ouazzani, F
    TETRAHEDRON-ASYMMETRY, 1998, 9 (13) : 2329 - 2332