TY - JOUR
T1 - A convenient synthesis of (2s,3r,6s,7z)- and (2r,3s,6s,7z)-2,3-epoxy- 7,10-bisaboladiene, the sex pheromones of the southern green stink bug (nezara viridula)
AU - Kuwahara, Shigefumi
AU - Itoh, Daisuke
AU - Leal, Walter Soares
AU - Kodama, Osamu
PY - 1998/9/17
Y1 - 1998/9/17
N2 - (2S,3R,6S,7Z)-2,3-Epoxy-7,10-bisaboladiene, a sex pheromone component of the southern green stink bug, Nezara viridula (L.) was synthesized stereoselectively in four steps (19% overall yield) from (S)-4-methyl-3- cyclohexene-1-carboxylic acid. This epoxy bisaboladiene was converted in three more steps (64% yield) to its (2R,3S,6S,7Z)-isomer, another sex pheromone component of the southern green stink bug, by inverting the configuration of the epoxide ring.
AB - (2S,3R,6S,7Z)-2,3-Epoxy-7,10-bisaboladiene, a sex pheromone component of the southern green stink bug, Nezara viridula (L.) was synthesized stereoselectively in four steps (19% overall yield) from (S)-4-methyl-3- cyclohexene-1-carboxylic acid. This epoxy bisaboladiene was converted in three more steps (64% yield) to its (2R,3S,6S,7Z)-isomer, another sex pheromone component of the southern green stink bug, by inverting the configuration of the epoxide ring.
KW - Olefination
KW - Pheromones
KW - Sulfur compound
KW - Terpenes and terpenoids
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U2 - 10.1016/S0040-4020(98)00696-6
DO - 10.1016/S0040-4020(98)00696-6
M3 - Article
AN - SCOPUS:0032541592
VL - 54
SP - 11421
EP - 11430
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 38
ER -