New approach to aphidicolin and total asymmetric synthesis of unnatural (11R)-(-)-8-epi-11-hydroxyaphidicolin by tandem transannular Diels-Alder/aldol reactions |
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| Authors: | Bélanger G Deslongchamps P |
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| Institution: | Laboratoire de synthèse organique, Département de chimie, Institut de Pharmacologie, Université de Sherbrooke, Fleurimont, Québec, Canada J1H 5N4. |
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| Abstract: | The 8-epiaphidicolane skeleton (3) was formed in one key reaction by highly diastereoselective tandem transannular Diels-Alder (TADA)-aldol reactions from the trans-trans-cis trienic macrocycle (4). The unnatural derivative (11R)-(-)-8-epi-11-hydroxyaphidicolin (2) was thus constructed, and an original solution to the C16 functionalization problem of many aphidicolin (1) syntheses is presented. |
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