Concise synthesis of (+)-fastigiatine12. Issue 1 (6th October 2015)

• Record Type: Journal Article
• Authors: Samame, Renzo A.; Owens, Christina M.; Rychnovsky, Scott D.
• Is Part Of: Chemical science. Volume 7:Issue 1(2016:Jan.)
• Page Start: 188
• Page End: 190
• Publication Date: 2015-10-06
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/c5sc03262h
• Languages: English
• ISSNs: 2041-6520

Abstract

Abstract : Biomimetic transannular Mannich cyclization led to (+)-fastigiatine. Abstract : (+)-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.