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Synthesis of All the Stereoisomers of 7‐Methylheptadecane and 7,11‐Dimethylheptadecane, the Female Sex Pheromone Components of the Spring Hemlock Looper and the Pitch Pine Looper
Author(s) -
Shirai Yasuo,
Seki Masanori,
Mori Kenji
Publication year - 1999
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199911)1999:11<3139::aid-ejoc3139>3.0.co;2-8
Subject(s) - chemistry , pheromone , sex pheromone , citronellol , cabbage looper , stereochemistry , enantiomer , botany , western hemlock , pest analysis , biology , geraniol , chromatography , trichoplusia , essential oil , noctuidae
All the stereoisomers of 7‐methylheptadecane ( 1 ) and 7,11‐dimethylheptadecane ( 2 ) were synthesized by starting from the enantiomers of citronellol ( 3 ) and methyl 3‐hydroxy‐2‐methylpropanonate ( 8 ), respectively. A short synthesis of meso ‐7,11‐dimethylheptadecane [(7 R ,11 S )‐ 2 ] was achieved starting from meso ‐2,6‐dimethylheptanedioic acid [(2 R ,6 S )‐ 21 ]. A mixture of ( S )‐ 1 and (7 R ,11 S )‐ 2 is the pheromone of the spring hemlock looper moth ( Lambdina athasaria ) and the pitch pine looper moth ( L. pellucidaria ).