Publisher： John Wiley & Sons Inc
E-ISSN： 1099-0690|2015|15|3240-3250
ISSN： 1434-193x
Source： EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, Vol.2015, Iss.15, 2015-05, pp. : 3240-3250
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Abstract
AbstractTotal syntheses of the erythrina alkaloids (±)‐8‐oxo‐erythrinine and (±)‐8‐oxo‐erythraline have been developed, based on a substrate‐controlled intramolecular 6‐exo‐trig selective radical spirocyclization that establishes the quaternary center of the B‐rings. An improved total synthesis of (±)‐clivonine has also been reported, based on an intramolecular 6‐endo‐trig free‐radical cyclization of a highly functionalized enamide, and a biomimetic ring‐switch of a lycorine‐type intermediate. These endo/exo‐selective sequences enabled us to rapidly assemble two different complex alkaloids from a common building block in an economical fashion.
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