The marine macrolide bryostatin 7 is prepared in 20 steps (longest linear sequence) and 36 total steps. A total of 5 C-C bonds are formed using hydrogenative methods. The present approach represents the most concise synthesis of any bryostatin reported, to date, setting the stage for practical syntheses of simplified functional analogues.
The 14-membered macrolide 6-deoxyerythronolide B is prepared in 14 steps (longest linear sequence) and 20 total steps. Two different methods for alcohol CH-crotylation via transfer hydrogenation are deployed for the first time in target-oriented synthesis. Enyne metathesis is used to form the 14-membered ring. The present approach represents the most concise construction of any erythronolide reported, to date.
Rings within rings: The total synthesis of (+)‐neopeltolide was accomplished by employing an intramolecular Prins macrocyclization of an aldehydic homoallylic alcohol intermediate (see scheme).
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