TY - JOUR
T1 - Synthesis of racemic brevioxime and related model compounds
AU - Clive, Derrick L.J.
AU - Hisaindee, Soleiman
PY - 2000/8/11
Y1 - 2000/8/11
N2 - The synthesis, in racemic form, of the insect juvenile hormone inhibitor brevioxime (1) is described, as well as exploratory studies that led to the related model compounds 14 and 15a. The route to 1 involves Ag+-mediated coupling of the amine derived from 20 with the β-keto thioester 32. Acid treatment of the coupled product 33 led by acetal hydrolysis, cyclization, and desilylation to 34a,b, from which 1 was reached by oxidation and conversion into the oxime. In the synthesis of the amino component 20, a known, but unusual, reduction was used for converting a nitrile into an amine hydrochloride.
AB - The synthesis, in racemic form, of the insect juvenile hormone inhibitor brevioxime (1) is described, as well as exploratory studies that led to the related model compounds 14 and 15a. The route to 1 involves Ag+-mediated coupling of the amine derived from 20 with the β-keto thioester 32. Acid treatment of the coupled product 33 led by acetal hydrolysis, cyclization, and desilylation to 34a,b, from which 1 was reached by oxidation and conversion into the oxime. In the synthesis of the amino component 20, a known, but unusual, reduction was used for converting a nitrile into an amine hydrochloride.
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U2 - 10.1021/jo0003551
DO - 10.1021/jo0003551
M3 - Article
C2 - 10956473
AN - SCOPUS:0034637487
SN - 0022-3263
VL - 65
SP - 4923
EP - 4929
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 16
ER -