Benzannulation for the Regiodefined Synthesis of 2-Alkyl/Aryl-1-naphthols: Total Synthesis of Arnottin I

D Mal, AK Jana, P Mitra, K Ghosh

Index: Mal, Dipakranjan; Jana, Amit Kumar; Mitra, Prithiba; Ghosh, Ketaki Journal of Organic Chemistry, 2011 , vol. 76, # 9 p. 3392 - 3398

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Citation Number: 37

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.