Insect antifeedants. 1. Diels-Alders approach to the synthesis of ajugarin I

As a part of a programme on the use of sugar-based dienes in the synthesis of bioactive molecules, we have prepared a few pairs of cis and trnns Diels-Alder adducts (1-6) of 2substituted p-benzoquinones and substituted glucofuranodienes.'S2 It was necessary to differentiate between these cis and trans isomers in order to process them to the target molecules. The need for the development of a technique more sensitive than NMR spectroscopy3 to differentiate between these isomers was felt as some of these isomers were formed in low yields. No clear-cut differences could be observed in the electron ionization (EI) and chemical ionization (CI) mass spectra of 1 4 . In view of the fact that in solution, chelation with alkali metal ions such as Li' preferentially occurs on one of the c a r b o n y l~~*~ it was thought that fast atom bombardment (FAB) using Li' or N a f for cationization could possibly differentiate between these isomers. Alkali ion attachment followed by collisional activation (CA) has been used to differentiate between isomers and also to determine linkage positions in sugar^.^-^

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Insect antifeedants. 1. Diels-Alders approach to the synthesis of ajugarin I

Cited by 11 publications

References 4 publications

ChemInform Abstract: INSECT ANTIFEEDANTS. PART 1. DIELS‐ALDER APPROACH TO THE SYNTHESIS OF AJUGARIN I

ChemInform Abstract: INSECT ANTIFEEDANTS. PART 1. DIELS‐ALDER APPROACH TO THE SYNTHESIS OF AJUGARIN I

ChemInform Abstract: Synthesis of Spiro Compounds as Medicinal Agents; New Opportunities for Drug Design and Discovery. Part I: A Review

Collosional activation spectra of Li⁺ and Na⁺ cationized Diels–Alder adducts of substituted p‐benzoquinones and glucofuranodienes

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Insect antifeedants. 1. Diels-Alders approach to the synthesis of ajugarin I

Cited by 11 publications

References 4 publications

ChemInform Abstract: INSECT ANTIFEEDANTS. PART 1. DIELS‐ALDER APPROACH TO THE SYNTHESIS OF AJUGARIN I

ChemInform Abstract: INSECT ANTIFEEDANTS. PART 1. DIELS‐ALDER APPROACH TO THE SYNTHESIS OF AJUGARIN I

ChemInform Abstract: Synthesis of Spiro Compounds as Medicinal Agents; New Opportunities for Drug Design and Discovery. Part I: A Review

Collosional activation spectra of Li+ and Na+ cationized Diels–Alder adducts of substituted p‐benzoquinones and glucofuranodienes

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Collosional activation spectra of Li⁺ and Na⁺ cationized Diels–Alder adducts of substituted p‐benzoquinones and glucofuranodienes