Efficient Synthesis of Diospyrol via Suzuki-Miyaura and Modified in situ Cross-Coupling

Poolsak Sahakitpichan; Nopporn Thasana; Somsak Ruchirawat

doi:10.1055/s-2005-872176

PAPER

Efficient Synthesis of Diospyrol via Suzuki-Miyaura and Modified in situ Cross-Coupling

Poolsak Sahakitpichan^a, Nopporn Thasana^a, Somsak Ruchirawat*^a,b
^a Chulabhorn Research Institute, Vipavadee Rangsit Highway, Bangkok 10210, Thailand
Fax: +66(2)5742027; e-Mail: somsak@cri.or.th;
^b Programme on Research and Development of Synthetic Drugs, Institute of Science and Technology for Research and Development, Mahidol University, Salaya Campus, Nakorn Pathom 73170, Thailand

Abstract

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Abstract

Tetramethoxydiospyrol was synthesized via Suzuki-Miyaura cross-coupling of the two key intermediates, halonaphthalene and naphthaleneboronic acid derivatives, which were derived from the same naphthol. Moreover, the product could be conveniently obtained by a one-pot modified in situ Suzuki coupling. The naphthol was synthesized via the cyclization of ortho-allylbenzamide intermediate.

Key words

biaryls - Suzuki-Miyaura cross-coupling - metalation - diospyrol

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References

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