Total synthesis of natural (?)- and unnatural (+)-Melearoride A |
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| Authors: | Carson W Reed Mark G Fulton Kellie D Nance Craig W Lindsley |
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| Institution: | 1. Department of Chemistry, Vanderbilt University, Nashville, TN 37232-6600, USA;2. Department of Pharmacology, Vanderbilt Center for Neuroscience Drug Discovery, Vanderbilt University, Nashville, TN 37232-6600, USA |
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| Abstract: | This communication details the first total synthesis of the 13-membered macrolide, (?)-Melearoride A, as well as unnatural (+)-Melearoride A. The synthesis features a concise 13 step synthesis (11 steps longest linear sequence) that offers flexible stereo-control and multiple opportunities for unnatural analog synthesis to delve into antifungal SAR. The route features a cuprate addition, an Evans asymmetric alkylation, and a ring-closing metathesis (RCM) to close the 13-membered macrocyclic core. |
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| Keywords: | Melearoride A Total synthesis Macrolides Asymmetric alkylation |
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