Electrophilic C12 building blocks for alkaloids: formal total synthesis of (+/-)-maritidine.
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.
Roe
Caroline
C
Wolfson Materials and Catalysis Centre, School of Chemical Sciences and Pharmacy University of East Anglia, Norwich NR4 7TJ, UK.
Stephenson
G Richard
GR
D047151:Amaryllidaceae Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010946:Plants, Medicinal / Q000737:chemistry; D013237:Stereoisomerism
D047151:Amaryllidaceae Alkaloids; D006576:Heterocyclic Compounds, 4 or More Rings; C476903:maritidine