An Efficient Synthesis of a Potential (−)‐Reserpine Intermediate from (−)‐Shikimic Acid of the Chiral Pool
Authors:
- 16 July 2007
- journal article
- research article
- Published by Wiley in Helvetica Chimica Acta
- Vol. 90 (7) , 1366-1372
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.Keywords
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