A Concise and Convenient Synthesis of dl-proto-Quercitol and dl-gala-Quercitol via Ene Reaction of Singlet Oxygen Combined with [2 + 4] Cycloaddition to Cyclohexadiene

Photooxygenation of 1,4-cyclohexadiene afforded hydroperoxy endoperoxides 3 and 4 in a ratio of 88:12. Reduction of 3 with LiAlH4 or thiourea followed by acetylation of the hydroxyl group and KMnO4 oxidation of the double bond gave proto-quercitol 10b. Application of the same reaction sequences to 4...

Full description

Saved in:
Bibliographic Details
Published inJournal of organic chemistry Vol. 62; no. 8; pp. 2453 - 2457
Main Authors Salamci, Emine, Seçen, Hasan, Sütbeyaz, Yasar, Balci, Metin
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 18.04.1997
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
MICROBIAL OXIDATION
CONDURITOL-F
STEREOSPECIFIC SYNTHESIS
BENZENE
CYCLITOLS
BIOCATALYSIS
Online AccessGet full text

Cover

More Information
Summary:Photooxygenation of 1,4-cyclohexadiene afforded hydroperoxy endoperoxides 3 and 4 in a ratio of 88:12. Reduction of 3 with LiAlH4 or thiourea followed by acetylation of the hydroxyl group and KMnO4 oxidation of the double bond gave proto-quercitol 10b. Application of the same reaction sequences to 4 resulted in the formation of gala-quercitol 14. Quercitols were easily obtained by ammonolysis of acetate derivatives in MeOH. The outcome of dihydroxylation reactions were supported by conformational analysis.
Bibliography:Dedicated to Professor Waldemar Adam on the occasion of his 60th birthday.
Abstract published in Advance ACS Abstracts, April 1, 1997.
istex:3ED70883B60F5098EE4D570D223AE634357511EB
ark:/67375/TPS-BRLMTW57-K
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/jo962092+