The first total synthesis of natural grenadamide.
A concise, high yielding route to the naturally occurring enantiomer of grenadamide utilizing a 3,6-disubstituted 1,2-dioxine starting material is presented. The route allows for ease in synthesizing grenadamide derivatives varying at cyclopropyl carbons 2 and 3, with access to both enantiomers. Evidence for phosphorus-assisted deprotonation of 1,2-dioxines is also discussed.
Avery
Thomas D
TD
Department of Chemistry, University of Adelaide, South Australia 5005, Australia.
Culbert
Julie A
JA
Taylor
Dennis K
DK
D000577:Amides / Q000138:chemical synthesis*; D003521:Cyclopropanes / Q000138:chemical synthesis*; D010758:Phosphorus; D013237:Stereoisomerism
D000577:Amides; D003521:Cyclopropanes; C112731:grenadamide; D010758:Phosphorus; C030797:cyclopropane