Alkyne‐Mediated Approach to the Synthesis of (4R,5R)‐5‐Hydroxy‐4‐decanolide and (−)‐Muricatacin |
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| Authors: | Chada Raji?Reddy Devatha Suman Nagavaram Narsimha?Rao |
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| Institution: | 1. Division of Natural Product Chemistry, CSIR‐Indian Institute of Chemical Technology, Hyderabad 500 007, India (phone: +91‐40‐27191885;2. fax: +91‐40‐27160512);3. Academy of Scientific and Innovative Research, New Delhi 110 001, India |
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| Abstract: | The asymmetric synthesis of two naturally occurring 5‐hydroxy‐γ‐butyrolactones, (4R,5R)‐5‐hydroxy‐4‐decanolide ( 1a ) and (?)‐muricatacin ( 2 ), is described using a general alkyne‐mediated strategy. The key steps involved are Sonogashira coupling for the desired carbon‐chain extension followed by Sharpless asymmetric dihydroxylation to construct the hydroxy‐lactone framework. |
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| Keywords: | Alkynes Butyrolactones (4R 5R)‐5‐Hydroxy‐4‐decanolide (− )‐Muricatacin Sharpless asymmetric dihydroxylation Sonogashira coupling |
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