Total synthesis of malyngamide X and its 7′S-epi isomer |
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| Authors: | Suchada Suntornchashwej Minoru Isobe |
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| Institution: | a Laboratory of Organic Chemistry, Graduate School of Bioagricultural Sciences and Institute of Advanced Research, Nagoya University, Chikusa, Nagoya 464-8601, Japan
b Center for Bioactive Natural Products from Marine Organisms and Endophytic Fungi (BNPME), Faculty of Pharmaceutical Sciences, Chulalongkorn University, Bangkok 10330, Thailand |
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| Abstract: | Stereoselective syntheses of malyngamide X (1) and its 7′(S)-epimer are described. A Lewis acid (Et2AlCl) mediated anti-aldol reaction was employed to generate the stereocenters C-7 and C-8. The route is convergent and provides a convenient access to the synthesis of structural variants of malyngamide X. Stereochemistry at C-7′ in the molecules of natural and synthetic 1, and 7′(S)-epi1 was confirmed by NMR chiral solvation experiments. |
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