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Paper | Regular issue | Vol 78, No. 3, 2009, pp.749-755
Published online, 19th November, 2008
DOI: 10.3987/COM-08-11574
Concise Synthesis of Xyloketal C Analogues

Yan Huang and Yong-Cheng Lin*

*School of Chemistry and Chemical Engineering, Sun Yat-Sen University, Guangzhou 510275, China

Abstract

The synthesis of xyloketal C analogues 12-methylxyloketal C(8) and 12-dehydroxylxyloketal C(11) have been accomplished in three steps, which featured the radical cyclisation as the key step. This is the shortest approach to construct the B C ring systems of the type of ketal skeleton reported to date. The structures of title compounds were elucidated by spectroscopic data and X-ray structure analysis. The final radical cyclisations give mainly the cis-fused anti-substituted stereoisomers.