Synthesis of racemic brevioxime and related model compounds

Derrick L.J. Clive, Soleiman Hisaindee

Research output: Contribution to journalArticlepeer-review

16 Citations (Scopus)


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.

Original languageEnglish
Pages (from-to)4923-4929
Number of pages7
JournalJournal of Organic Chemistry
Issue number16
Publication statusPublished - Aug 11 2000
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry


Dive into the research topics of 'Synthesis of racemic brevioxime and related model compounds'. Together they form a unique fingerprint.

Cite this