Tue, 21 Nov 2017

Synthesis of Semi-tetracycline Backbone Through Diels-Alder Reaction of 2,3-Dimethylbutadiene or Cyclopentadiene With 1,4-Benzoquinones

Zackaria Fataftah1, Raad Al-Hamdany1, Kanan M. Wahedy*2

1 Department of Chemistry, Faculty of Science –Yarmouk University- Irbid (Jordan)

2.Department of Pharmaceutical Chemistry, Faculty of pharmacy–Al-Azhar University-Gaza (Palestine)


ABSTRACT

Two main semi-tetracycline systems were synthesized. The strategy of such synthesis depends on the transformation of aroyl-1,4-benzoquinone to aroylketal-1,4-benzoquinone causes a regiocontrol addition of cyclopentadiene and 2,3-butadiene to the unsubstituted side of the quinone. These ketal adducts were hydrolyzed using the acidic media; as a result deketalization and enolization in one step give the semi-tetracycline system. The structures of these compounds were confirmed by NMR, IR, MS and elemental analysis.

Keywords: - Diels-Alder, semi-tetracycline, Benzoquinone,Butadiene, Cyclopentadiene.


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