Total synthesis of (−)-diospongin A and (+)-cryptofolione via asymmetric aldol reaction |
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Authors: | Rayala Naveen KumarH.M. Meshram |
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Affiliation: | Organic chemistry Division—I, Indian Institute of Chemical Technology, Hyderabad 500 007, India |
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Abstract: | Stereoselective synthesis of two distinctive pyranone skeletons diospongin A and cryptofolione has been described based on an asymmetric aldol reaction starting from Chan’s diene. The synthetic strategy involves the enantioselective Mukaiyama aldol, diastereoselective reduction of δ-hydroxy-β-keto ester, a tandem sequence of deprotection, and intramolecular oxa-Michael reaction to obtain diospongin A and an asymmetric allylation and lactone formation using ring-closing metathesis reaction to obtain cryptofolione. |
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Keywords: | Diospongin A Cryptofolione Chan&rsquo s diene Asymmetric Mukaiyama aldol Diastereoselective reduction Ring-closing metathesis |
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