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Synthesis 2011(7): 1137-1141  
DOI: 10.1055/s-0030-1258456
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

An Efficient Convergent Access to Spiroketal Segment of (+)-Spiroxaline Methyl Ether

Mandeep Singh, Narshinha P. Argade*
Division of Organic Chemistry, National Chemical Laboratory (CSIR), Pune 411008, India
Fax: +91(20)25902629; e-Mail: np.argade@ncl.res.in;
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Publication History

Received 15 December 2010
Publication Date:
02 March 2011 (online)

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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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