Current time in Korea 08:30 Oct 20 (Fri) Year 2017 KCS KCS Publications
KCS Publications
My Journal Log In Register
HOME > Search > Browsing(BKCS) > Archives

Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 28, Number 9
BKCSDE 28(9)
September 20, 2007 

 
Title
Efficient Construction of Quaternary Carbon: Stereocontrolled Synthesis of Novel Abacavir Analogue
Author
Aihong Kim, Joon Hee Hong*
Keywords
Quaternary carbon, Abacavir, Claisen rearrangement, Ring-closing metathesis
Abstract
This paper discusses the racemic and stereoselective synthetic route for novel 4'α -methyl and 6'α -methyl analogues of abacavir. The quaternary carbon at the 4'-position of carbocyclic nucleoside was installed successfully via a Claisen rearrangement. The stereocontrolled construction of a methyl group in the 6'α - position was directed through the Felkin-Anh rule. A Bis-vinyl compound 9 was cyclized successfully using Grubbs’ catalyst II to provide a carbocycle nucleus for the target compound. The synthesized compound 15 showed moderate anti-HIV activity (EC50 = 10.67 μM, MT-4 cell lines).
Page
1545 - 1548
Full Text
PDF