Application of the BHQ benzannulation reaction to the synthesis of benzo-fused coumarins

TETRAHEDRON LETTERS

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Article

Hutchings, Michael G.¹  Quayle, Peter¹ 

[1] Univ Manchester, Sch Chem, DyStar UK Ltd, Manchester M13 9PL, Lancs, England

关键词: ATRC;    Kharasch;    Cyclisation;    Radical;    Copper;    Carbene;    Benzannulation;    Lactone;   

DOI  :  10.1016/j.tetlet.2009.03.077

来源: Elsevier

【 摘 要 】

A new approach to the synthesis of the 6H-benzo[d]naphthal[,2-b]pyran-6-one ring system present in the gilvocarcin family of antibiotics is described. The key feature of this approach is the application of a new benzannulation strategy (the 'BHQ Reaction') whereby readily available ortho-allylaryl trichloroacetates are transformed into naphthalene derivatives via a cascade of reactions involving an initial ATRC reaction followed by the extrusion of CO2. (C) 2009 Elsevier Ltd. All rights reserved.

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