Stereoselective total synthesis of (+)-(6R,2′S)-cryptocaryalactone and (−)-(6S,2′S)-epi cryptocaryalactone |
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| Authors: | Gowravaram Sabitha V. Bhaskar S. Siva Sankara Reddy J.S. Yadav |
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| Affiliation: | aOrganic Division I, Indian Institute of Chemical Technology, Hyderabad 500 007, India |
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| Abstract: | The total synthesis of (+)-(6R,2′S)-cryptocaryalactone and (−)-(6S,2′S)-epi cryptocaryalactone is reported based on stereoselective reduction of δ-hydroxy β-keto ester to install 1,3-polyol system, cis Wittig olefination, and lactonization as the key steps. The synthesis of (−)-(6S,2′S)-epi cryptocaryalactone is also reported using syn-benzylidene acetal formation and a preferential Z-Wittig olefination reaction and lactonization as the key steps. |
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| Keywords: | α ,β -Unsaturated δ -lactone Base catalyzed conjugate addition Z-Wittig olefination Stereoselective reduction cis Wittig olefination 1,3-Polyol |
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