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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 38, 2008 - Issue 10
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Original Articles

Synthetic Studies toward C3‐C9 Segment of Soraphen A

Pages 1541-1552 | Received 08 Aug 2007, Published online: 24 Apr 2008
 

Abstract

The ring‐closure metathesis of the diene (2S,3R,4S)‐1‐(tert‐butyldiphenylsilyloxy)‐2,4‐dimethylhex‐5‐en‐3‐yl acrylate produced the dihydropyrone with the correct stereochemistry for Soraphen A synthesis. The C2,C3 stereocenters were introduced by the addition of the (Z)‐crotyl‐n‐butylstannane to the β‐alkoxyaldehyde(S)‐3‐(benzyloxy)‐2‐methylpropanal in presence of TiCl4 as a chelating catalyst to give the desired anti,syn homoallyic alcohol (2S,3R,4S)‐1‐(tert‐butyldiphenylsilyloxy)‐2,4‐dimethylhex‐5‐en‐3‐ol.

Acknowledgments

Financial support for this work was provided by the National Institutes of Health (GM‐42641) and the Marquette University Graduate School. The author thanks Dr. William A. Donaldson for his encouragement.

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