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. 2010 Oct 1;12(19):4304-7.
doi: 10.1021/ol101744h.

Pericyclic reaction of a zwitterionic salt of an enedione-diazoester. A novel strategy for the synthesis of highly functionalized resorcinols

Yu Liu  1 , Kanwarpal Bakshi, Peter Zavalij, Michael P Doyle
Affiliations

Pericyclic reaction of a zwitterionic salt of an enedione-diazoester. A novel strategy for the synthesis of highly functionalized resorcinols

Yu Liu et al. Org Lett. .

Abstract

Enedione-diazoesters formed from 3-TBSO-2-diazo-3-butenoates undergo base-catalyzed pericyclization that with dinitrogen extrusion and methyl migration provide a novel and efficient route to 2-carboalkoxyresorcinols. Intercepting the intermediate enolate anion with methyl vinyl ketone leads to the corresponding 4-substituted 2-carboalkoxyresorcinol and suggests generalization of this methodology.

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Figures

Scheme 1
Scheme 1
Mukaiyama-Michael Reactions of TBSO-Substituted Vinyldiazoacetate 1
Scheme 2
Scheme 2
Mukaiyama-Michael Reaction with 4-Methoxy-3(E)-buten-2-one
Scheme 3
Scheme 3
Reactions of Methyl 2-Diazo-3,7-dioxo-5(E)-octenoate
Scheme 4
Scheme 4
Base-catalyzed Pericyclization-rearrangement of 4
Figure 1
Figure 1
X-ray structure of 1,2-Diazepine 13b.
Scheme 5
Scheme 5
Pathway to 1,2-Diazepines 13
Scheme 6
Scheme 6
Synthesis of Atraric Acid Derivative
Scheme 7
Scheme 7
Michael Addition/Pericyclization/Rearrangement
See this image and copyright information in PMC

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