Electrophilic C12 building blocks for alkaloids: Formal total synthesis of (±)-maritidine

Caroline Roe, G. Richard Stephenson

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Silyl-protected benzyl alcohol derivatives and the salt 1 are used to form ortho-substituted C-12 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.
Original languageEnglish
Pages (from-to)189-192
Number of pages4
JournalOrganic Letters
Issue number2
Publication statusPublished - 2008

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