Synthesis of the C12-C19 fragment of (+)-peloruside A through a diastereomer-discriminating RCM reaction.
[reaction: see text]. A short and efficient asymmetric synthesis of the C12-C19 fragment of the cytotoxic macrolide (+)-peloruside A has been achieved via a highly diastereomer-discriminating RCM of alpha-branched but-3-enoate ester of a methallylic alcohol derived from hydrolytically resolved (S)-(-)-propylene oxide.
Roulland
Emmanuel
E
Institut de Chimie des Substances Naturelles, CNRS, avenue de la Terrasse, 91198 Gif-sur-Yvette, France.
Ermolenko
Mikhail S
MS
D000818:Animals; D000970:Antineoplastic Agents / Q000032:analysis / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000032:analysis / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D004852:Epoxy Compounds / Q000737:chemistry; D007783:Lactones / Q000032:analysis / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D015394:Molecular Structure; D011161:Porifera / Q000737:chemistry; D013237:Stereoisomerism
D000970:Antineoplastic Agents; D019086:Bridged Bicyclo Compounds, Heterocyclic; D004852:Epoxy Compounds; D007783:Lactones; C414085:peloruside A; C009068:propylene oxide