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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 

Efficient Construction of Quaternary Carbon: Stereocontrolled Synthesis of Novel Abacavir Analogue
Aihong Kim, Joon Hee Hong*
Quaternary carbon, Abacavir, Claisen rearrangement, Ring-closing metathesis
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).
1545 - 1548
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