Catalytic asymmetric claisen rearrangement in natural product synthesis: synthetic studies toward (-)-xeniolide F.
[chemical reaction: see text]. The catalytic asymmetric Claisen rearrangement (CAC) of a highly substituted and functionalized alpha-alkoxycarbonyl-substituted allyl vinyl ether has been exploited to gain access to an advanced building block for the projected total synthesis of (-)-xeniolide F, the enantiomer of a xenicane diterpene isolated from a coral of the genus Xenia.
Pollex
Annett
A
Institut für Organische Chemie, Technische Universität Dresden, D-01062 Dresden, Germany.
Hiersemann
Martin
M
D000818:Animals; D037421:Anthozoa / Q000737:chemistry; D002384:Catalysis; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000737:chemistry*
D004224:Diterpenes; D014753:Vinyl Compounds; C461725:xeniolide F; C100195:vinyl ether