Concise synthesis of (+)-fastigiatine
- Author(s): Samame, RA
- Owens, CM
- Rychnovsky, SD
- et al.
Published Web Locationhttps://doi.org/10.1039/c5sc03262h
(+)-Fastigiatine was assembled in six steps from (R)-5-methylcyclohex-2-en-1-one. Intermolecular Diels-Alder reaction introduced most of the carbon atoms for the target. The two Boc-protected nitrogen atom building blocks were introduced by a Suzuki coupling and a cuprate addition. A biomimetic transannular Mannich reaction generated the two quaternary centers at a late stage. Each step builds core bonds, and combined with a minimalist protecting group strategy, this approach led to a very concise synthesis.
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