Synthesis of C-seco limonoid model insect antifeedants related to ochinolide

A short and selective synthesis of C-seco limonoid model insect antifeedant related to ochinolide was accomplished in seven steps from alpha-cyclocitral. The key steps an the electrocyclization of a P-acyl divinyl ketone induced by perchloric acid, and a selective retroclaisen reaction. A rare examp...

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Bibliographic Details
Published inSynlett no. 12; pp. 1372 - 1374
Main Authors Mateos, AF, de la Nava, EM, Coca, GP, Silvo, AR, Gonzalez, RR
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.12.1998
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
antifeedant
perchloric acid
retroclaisen reaction
limonoids
Nazarov reaction
NAZAROV CYCLIZATION
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Summary:A short and selective synthesis of C-seco limonoid model insect antifeedant related to ochinolide was accomplished in seven steps from alpha-cyclocitral. The key steps an the electrocyclization of a P-acyl divinyl ketone induced by perchloric acid, and a selective retroclaisen reaction. A rare example of atropisomerism was found in the trisubstituted cyclopentenone 6 key intermediate.
ISSN:0936-5214
DOI:10.1055/s-1998-1962