Abstract
The Wittig reaction of 3-isopropyl-4-methoxybenzaldehyde and 2,3-dimethylbenzylphosphonium bromide afforded the corresponding stilbene mixture 16. Oxidative photocyclization of stilbene 16 with iodine facilitated the first total synthesis of 7-isopropyl-6-methoxy-1,2-dimethylphenanthrene, multicaulin (1). The O-demethylation of 1 with BBr3 afforded the 7-isopropyl-1,2-dimethylphenanthren-6-ol, O-demethylmulticaulin (2).
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Benzaldehydes / chemistry*
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Cyclization
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Molecular Structure
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Organophosphorus Compounds / chemistry*
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Oxidation-Reduction
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Phenanthrenes / chemical synthesis*
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Phenanthrenes / chemistry
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Stilbenes / chemistry*
Substances
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2,3-dimethylbenzylphosphonium bromide
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3-isopropyl-4-methoxybenzaldehyde
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Benzaldehydes
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Organophosphorus Compounds
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Phenanthrenes
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Stilbenes
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multicaulin