Intramolecular Cyclization During Bromination of the Quinoline Alkaloid Haplophyllidine,Chemistry of Natural Compounds

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Intramolecular Cyclization During Bromination of the Quinoline Alkaloid Haplophyllidine
Chemistry of Natural Compounds ( IF 0.8 ) Pub Date : 2022-11-15 , DOI: 10.1007/s10600-022-03877-6
A U Ubaidullaev ₁ , V I Vinogradova ₁ , Sh N Zhurakulov _{1,

2} , N I Mukarramov ₁ , Kh M Bobakulov _{1,

3} , K A Turgunov ₁ , B Tashkhodzhaev ₁

Affiliation

Bromination of the furanoquinoline alkaloid haplophyllidine by molecular bromine and N-bromosuccinimide was accompanied by intramolecular cyclization to form mixtures of new compounds containing additional penta-, hexa-, and spirocyclic rings incorporating the prenyl group of haplophyllidine. The structures and absolute configurations of the chiral centers of all four bromo-derivatives were elucidated using a combination of NMR spectroscopic methods and X-ray crystal structure analyses.

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