2-Propyl-, 5-propyl-, and 6-propylisoproterenols (2a, 2b, and Id, respectively) have been synthesized as models for polymer drug conjugates. Key intermediates were the propenylbenzaldehydes 3a-c. The (isopropylamino)phenethanol side chain was constructed from the aldehyde functionality by the method of Avery et al.2 The benzaldehyde 3b was prepared from 3,4-dihydroxybenzaldehyde (7) by selective alkylation at the 4-hydroxyl followed by Claisen rearrangement and benzylation of the phenolic hydroxyls. Selective alkylation at the 3-hydroxyl Approach to the Total Synthesis of Chlorothricolide: Synthesis of "7-epi-Bottom Half' and Its Union with "Top Half' Systems
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