jo5026404_si_003.cif (19.73 kB)
Construction of the Myrioneuron Alkaloids: A Total Synthesis of (±)-Myrioneurinol
dataset
posted on 2015-01-16, 00:00 authored by Anthony
J. Nocket, Yiqing Feng, Steven M. WeinrebA strategy
has been developed that culminated in a stereoselective
total synthesis of the tetracyclic antimalarial Myrioneuron alkaloid myrioneurinol. The synthesis relies on three highly diastereoselective
reactions, including an intramolecular chelation-controlled Michael
spirocyclization of an N-Cbz-lactam titanium enolate
to an α,β-unsaturated ester for construction of the A/D-ring
system and the attendant C5 (quaternary), C6 relative stereochemistry;
a malonate enolate conjugate addition to a nitrosoalkene in order
to install the appropriate functionality and establish the configuration
at C7; and an intramolecular aza-Sakurai reaction to form the B-ring
and the accompanying C9 and C10 stereocenters.
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C 9C 10 stereocentersintramolecularspirocyclizationnitrosoalkeneMyrioneuron AlkaloidsconfigurationfunctionalitystrategyConstructionesterstereochemistrysynthesisdiastereoselective reactionstetracyclic antimalarial Myrioneuron alkaloid myrioneurinolattendant C 5malonate enolate conjugate additionMyrioneurinolATotal Synthesisconstructionquaternary
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