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

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Roe, Caroline and Stephenson, G. Richard (2008) Electrophilic C12 building blocks for alkaloids: Formal total synthesis of (±)-maritidine. Organic Letters, 10 (2). pp. 189-192. ISSN 1523-7052

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Abstract

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.

Item Type: Article
Additional Information: Roe, Caroline Stephenson, G. Richard
Faculty \ School: Faculty of Science > School of Chemistry (former - to 2024)
UEA Research Groups: Faculty of Science > Research Groups > Chemistry of Materials and Catalysis
Faculty of Science > Research Groups > Synthetic Chemistry (former - to 2017)
Depositing User: Rachel Smith
Date Deposited: 29 Mar 2011 11:45
Last Modified: 13 Oct 2025 05:32
URI: https://ueaeprints.uea.ac.uk/id/eprint/27416
DOI: 10.1021/ol702550z

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