Rapid assembly of the bicyclo[5.3.1]undecenone core of penostatin F: a successive Diels-Alder/Claisen reaction strategy with an efficient stereochemical relay.
The first synthesis of the tricyclic core of Penostatin F (1) using a stereocontrolled Diels-Alder reaction and a Claisen rearrangement in succession has been achieved in nine steps from commercially available methyl acetoacetate and (E)-2-decenal. Penostatin F is a metabolite isolated from a fungal strain of Penicillium sp., OUPS-79, separated from the marine alga Enteromorphia intestinalis and exhibits significant cytotoxicity against cultured P388 Leukemia cells (ED(50) = 1.4 micromol/mL). [reaction: see text]
Barriault
Louis
L
Department of Chemistry, 10 Marie Curie, University of Ottawa, Ottawa, Ontario, Canada K1N 6N5. lbarriau@science.uottawa.ca
Ang
Patrick J A
PJ
Lavigne
Roch M A
RM
D000090:Acetoacetates / Q000737:chemistry; D000447:Aldehydes / Q000737:chemistry; D000818:Animals; D001578:Benzopyrans / Q000138:chemical synthesis* / Q000494:pharmacology; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000494:pharmacology; D003500:Cyclization; D004852:Epoxy Compounds / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
C096140:4,5-epoxy-2-decenal; D000090:Acetoacetates; D000447:Aldehydes; D001578:Benzopyrans; D019086:Bridged Bicyclo Compounds, Heterocyclic; D004852:Epoxy Compounds; C496162:penostatin F