Simple access to 5-carboalkoxy-2,3-dihydro-4H-pyran-4-ones via domino acylative electrocyclization: the first three step total synthesis of the dihydronaphthopyran-4-one class of natural products
作者： Andivelu Ilangovan , Palaniappan Sakthivel
DOI: 10.1039/C4RA11174E
关键词: Aromatization 、 Naphthalene 、 Intramolecular force 、 Total synthesis 、 Domino 、 Organic chemistry 、 Pyran 、 Ring (chemistry) 、 Chemistry
摘要: Intermolecular domino C-acylation/6π-oxaelectrocyclization between β-ketoesters and α,β-unsaturated acid chlorides took place readily in the presence of CaCl2 to afford a variety polysubstituted 5-carboalkoxy-2,3-dihydro-4H-pyran-4-ones, good yields. The products were successfully exploited as precursors, for simple efficient construction naphthalene fused pyran-4-one ring system. This intramolecular Friedel–Crafts acylative aromatization approach was useful synthesis phytogrowth inhibiting dihydronaphthopyranone class natural products.
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