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 resulta...

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Bibliographic Details
Published inSynthesis (Stuttgart) no. 9; pp. 1392 - 1402
Main Authors Brimble, Margaret A., Liu, Yen-Cheng (William), Trzoss, Michael
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 04.05.2007
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
STREPTOMYCES SP MJ929-SF2
AROMATIC SPIROKETAL SKELETON
BAEYER-VILLIGER OXIDATION
PURPUROMYCIN
DNA HELICASE
NAPHTHO
INHIBITOR
HELIQUINOMYCIN
DERIVATIVES
GAMMA-RUBROMYCIN
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Summary: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.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-2007-966016