A facile synthesis of aryl spirodioxines based on a 3H,3′H-2, 2′-spiro-bi(benzo[b][1,4]dioxine) skeleton
The synthesis of a series of 6,6-bisbenzannulated spiroketals containing a 3H,3′H-2,2′-spirobi(benzo[b][1,4]dioxine) ring system is reported. The key step involves addition of a monobenzyl-protected catechol to the epoxide unit of a glycidol bearing a benzyl-protected catechol. The resultant alcohol adduct is oxidized to a ketone that then undergoes hydrogenation and acid-catalyzed cyclization to produce the desired spirodioxines. Georg Thieme Verlag Stuttgart.
Brimble, Margaret A.,Liu, Yen-Cheng,Trzoss, Michael
p. 1392 - 1402
(2008/02/12)
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