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Synthesis 2011(7): 1137-1141
DOI: 10.1055/s-0030-1258456
DOI: 10.1055/s-0030-1258456
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New YorkAn Efficient Convergent Access to Spiroketal Segment of (+)-Spiroxaline Methyl Ether
Further Information
Received
15 December 2010
Publication Date:
02 March 2011 (online)
Publication History
Publication Date:
02 March 2011 (online)
Abstract
Starting from trimethylsilylacetylene, a facile synthesis of optically pure spiroketal unit of (+)-spiroxaline methyl ether has been described. The synthesis entails stepwise alkylation and acylation of an alkyne with two different readily available chiral building blocks followed by the reductive in situ regio- and stereoselective spiroketalization pathway.
Key words
alkyne - (R)-oxirane - (R)-γ-valerolactone - nucleophilic reactions - (+)-spiroketal segment synthesis
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