The Friedel−Crafts Allylation of a Prenyl Group Stabilized by a Sulfone Moiety:  Expeditious Syntheses of Ubiquinones and Menaquinones

The Friedel−Crafts Allylation of a Prenyl Group Stabilized by a Sulfone Moiety:  Expeditious Syntheses of Ubiquinones and Menaquinones

An efficient synthetic method for the protected p-hydroquinone compounds 4 containing the C5 trans allylic sulfone moiety has been developed by the direct Friedel−Crafts allylation of the protected dihydroquinone 2 with 4-chloro-2-methyl-1-phenylsulfonyl-2-butene (7a) or 4-hydroxy-2-methyl-1-phenyls...

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry Vol. 68; no. 20; pp. 7925 - 7927
Main Authors: Min, Jae-Hong, Lee, Jun-Sup, Yang, Jae-Deuk, Koo, Sangho
Format: Journal Article
Language:English
Published: Washington, DC American Chemical Society 03-10-2003
Subjects:
Chemistry
Exact sciences and technology
Noncondensed benzenic compounds
Organic chemistry
Preparations and properties
Lewis acid
Friedel Crafts reaction
Sulfone
Chemical synthesis
Allylic compound
Ethylenic compound
Allylation
Hydroquinone derivatives
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:An efficient synthetic method for the protected p-hydroquinone compounds 4 containing the C5 trans allylic sulfone moiety has been developed by the direct Friedel−Crafts allylation of the protected dihydroquinone 2 with 4-chloro-2-methyl-1-phenylsulfonyl-2-butene (7a) or 4-hydroxy-2-methyl-1-phenylsulfonyl-2-butene (7b). Expeditious total syntheses of coenzyme Q-10 and vitamin K2(20) have been demonstrated from these valuable key compounds 4a and 4b.
Bibliography:ark:/67375/TPS-NMGW9Q01-0
istex:5DD0EF8916DFD90B00FE1C26ACABA22B3432A261
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/jo0350155