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Electrophilic C12 building blocks for alkaloids: formal total synthesis of (+/-)-maritidine
Caroline Roe1, G Richard Stephenson
1Wolfson Materials and Catalysis Centre, School of Chemical Sciences and Pharmacy University of East Anglia, Norwich NR4 7TJ, UK.
Abstract:
Silyl-protected benzyl alcohol derivatives and the salt 1 are used to form ortho-substituted C12 electrophilic organoiron building blocks which are converted into a spirocyclic cyclohexenone to complete a formal total synthesis of (+/-)-maritidine (5). The choice of TBDPS protection was shown to be better than TIPS and compatible with ipso nucleophile addition to form a quaternary center. The reaction sequence is the first example of a successful application in the synthesis of an arylcyclohexadienyliron complex with an ortho-carbon substituent in the position required for Amaryllidaceae alkaloids of this type.
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