1220119-80-1Relevant academic research and scientific papers
Total synthesis of (± )-Haliclonacyclamine C
Smith, Brian J.,Sulikowski, Gary A.
supporting information; experimental part, p. 1599 - 1602 (2010/06/15)
"Chemical Equation Presented" (±)-Haliolonacyolamine C First In Its class: The synthesis of the tetracyclic alkylpiperidine marine alkaloid (±)-haliclonacyclamine C has been completed, with a longest linear sequence of 24 steps. The key transformations are the stereoselective hydrogenation of an unsaturated macrocyclic bis (piperidine) and a ring-closing alkyne metathesis reaction.
Synthesis and bioactivity of (±)-tetrahydrohaliclonacyclamine A
Smith, Brian J.,Qu, Tao,Mulder, Matthew,Noetzel, Meredith J.,Lindsley, Craig W.,Sulikowski, Gary A.
scheme or table, p. 4805 - 4810 (2010/08/06)
The total synthesis of tetrahydrohaliclonacyclamine A (5) is described. A key step involves the hydrogenation of an unsaturated bis-piperidine incorporated into a 17-membered macrocycle to provide the cis-syn-cis stereochemistry common to haliclonacyclamines A-D. The hydrogenation product is advanced to the title compound following a five-step reaction sequence. Tetrahydrohaliclonacyclamine A is shown to bind to a variety of ion channels/GPCRs and act as a muscarinic M1 antagonist.
