Towards Stereoselective Synthesis of the C(31)–C(39) and C(20)–C(27) Fragments of Phorboxazole A |
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| Authors: | Kammari Bal Raju Bejjanki Naveen Kumar Bandari Sampath Kumar Kommu Nagaiah |
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| Institution: | 1. Organic and Biomolecular Chemistry Division, Indian Institute of Chemical Technology, Hyderabad 500076, India (phone: +91‐40‐27191659;2. fax: +91‐40‐27193275) |
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| Abstract: | The stereoselective synthesis of the C(31)–C(39) and C(20)–C(27) fragments of phorboxazole A ( 1 ) was achieved from commercially available and inexpensive D ‐mannitol. Crimmins aldol reaction and a decarboxylative Claisen‐type reaction are the key steps for the C(31)–C(39) fragment, and L ‐proline‐catalyzed aldol reaction, Sharpless asymmetric epoxidation, and epoxide ring opening reaction with Gilman's reagent are the key steps for the C(20)–C(27) fragment of phorboxazole. |
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| Keywords: | Phorboxazole A D‐Mannitol Crimmins aldol reaction Aldol reaction L‐proline‐catalyzed Cytotoxic activity |
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