An Efficient Synthesis of a Potential (−)‐Reserpine Intermediate from (−)‐Shikimic Acid of the Chiral Pool |
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| Authors: | Jian Huang Fen‐Er Chen |
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| Institution: | Department of Chemistry, Fudan University, Shanghai, 200433, P.?R. China, (fax: +86‐21‐65643811) |
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| Abstract: | A highly stereoselective route to the polysubstituted chiral octahydrobenzofuran 12 , a potential synthon for the E‐ring core in the (?)‐reserpine synthesis, is described. The α‐bromo acetal 11 was obtained from inexpensive (?)‐shikimic acid ( 3 ) through a series of highly stereoselective chemical reactions (Scheme). Et3B/Bu3SnH‐Mediated intramolecular radical cyclization of 11 led to compound 12 with the required configuration. |
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| Keywords: | Reserpine Shikimic acid Stereoselective reactions Radical cyclization Chiral pool |
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