title: Total synthesis of stemaphylline N-oxide and related C9a-epimeric analogues.
abstract: Winning the relay: The first total synthesis of stemaphylline N-oxide has been completed utilizing a bistandem relay ring-closing-metathesis (RRCM) strategy, necessitated by the conformation of the requisite tetraene. This effort also gave unnatural 9a-epi-stemaphylline and 9a-epi-stemaphylline N-oxide.
authors: Department of Chemistry, Vanderbilt University, 7330 Stevenson Center, Station B 351822, Nashville, TN 37235 (USA).
authors: Michael L
authors: ML
authors: Schulte
authors: Mark L
authors: ML
authors: Turlington
authors: Sharangdhar S
authors: SS
authors: Phatak
authors: Joel M
authors: JM
authors: Harp
authors: Shaun R
authors: SR
authors: Stauffer
authors: Craig W
authors: CW
authors: Lindsley
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry*; D000475:Alkenes / Q000737:chemistry*; D003500:Cyclization; D008968:Molecular Conformation
chemical_list: D000470:Alkaloids; D000475:Alkenes; C550786:stemaphylline; C550787:stemaphylline-N-oxide
keywords: alkaloids; metathesis; stemaphylline; stemaphylline N‐oxide; total synthesis
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