Benzannulation for the regiodefined synthesis of 2-alkyl/aryl-1-naphthols: total synthesis of arnottin I |
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Authors: | Mal Dipakranjan Jana Amit Kumar Mitra Prithiba Ghosh Ketaki |
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Institution: | Department of Chemistry, Indian Institute of Technology, Kharagpur 721302, India. dmal@chem.iitkgp.ernet.in |
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Abstract: | The annulation of phthalides with α-alkyl/arylacrylates in the presence of LDA/LHMDS is shown to directly give alkyl/aryl-1-naphthols. The method involving a novel dealkoxycarbonylation obviates the regiochemical issues in the synthesis of polysubstituted naphthalenes, and it forms the key step in a three-step total synthesis of arnottin I, a naphthobenzopyranone natural product. |
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