Title : Intramolecular aldol cyclization of C-4-ulopyranosyl-2'-oxoalkanes controlled by steric effects. Asymmetric synthesis of substituted 8-oxabicyclo[3.2.1]octanones and -octenones and cyclopentenones.

Pub. Date : 2004 Oct 20

PMID : 15476708






2 Functional Relationships(s)
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1 Whereas C-2- and 4-ulopyranosyl compounds (C-2- and C-4-ulosides) can be converted to cyclopentenones under base conditions through beta-elimination and ring contraction, base-initiated beta-elimination of C-glycosyl 2"-aldehydes and 2"-ketones results in the formation of acyclic alpha,beta-unsaturated aldehydes or ketones. Ketones complement C2 Homo sapiens
2 Whereas C-2- and 4-ulopyranosyl compounds (C-2- and C-4-ulosides) can be converted to cyclopentenones under base conditions through beta-elimination and ring contraction, base-initiated beta-elimination of C-glycosyl 2"-aldehydes and 2"-ketones results in the formation of acyclic alpha,beta-unsaturated aldehydes or ketones. Ketones complement C2 Homo sapiens