Asymmetric total synthesis of (+)-gabosine C and (+)-4-epi-gabosine J using acetate migration and RCM reaction |
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Authors: | Balija Sivakrishna Shantanu Pal |
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Affiliation: | School of Basic Sciences, Indian Institute of Technology Bhubaneswar, Argul, Odisha, 752050, India |
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Abstract: | A concise, unified and stereoselective total synthesis of (+)-gabosine C and (+)-4-epi-gabosine J from a common polyhydroxylated cyclohexenol intermediate which was synthesized from readily available D-ribose has been described. The synthetic avenue includes stereoselective Grignard reaction, silyl ether deprotection followed by acetate migration, RCM reaction, oxidative diol cleavage, hydroxymethylation and oxidative rearrangement as key steps. |
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Keywords: | Corresponding author. Natural product Acetate migration Metathesis Cyclohexenol Oxidative rearrangement D-ribose |
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