Welch, Steven C.2022-02-082022-02-08197417371634https://hdl.handle.net/10657/8675Stereoselective total syntheses of (±)-longicyclene (1), ([plus-minus])-longicamphor (2A), and ([plus-minus])-longiborneol (2B) from tetrahydroeucarvone (21) via intermediate aldehyde 23 are discussed. The synthetic approach contains a reductive-cyclization reaction utilizing di isobutyl aluminum hydride to convert an enol-lactone to a bicyclic ketol. A new sequence of reactions is used to convert a cyclopropyl ketone intermediate to ([plus-minus])-longicyclene (1) without fragmentation. An attempt to apply a modification of the synthetic scheme used in the ([plus-minus])-longicyclene synthesis to the synthesis of (+)-cyclosativine (.5) is also presented.application/pdfenThis item is protected by copyright but is made available here under a claim of fair use (17 U.S.C. §107) for non-profit research and educational purposes. Users of this work assume the responsibility for determining copyright status prior to reusing, publishing, or reproducing this item for purposes other than what is allowed by fair use or other copyright exemptions. Any reuse of this item in excess of fair use or other copyright exemptions requires express permission of the copyright holder.Thesisreformatted digital