Concise synthesis of (+)-fastigiatine

(+)-Fastigiatine was assembled in six steps from ( )-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 tran...

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Bibliographic Details
Published in:Chemical science (Cambridge) 2016-01, Vol.7 (1), p.188-190
Main Authors: Samame, Renzo A, Owens, Christina M, Rychnovsky, Scott D
Format: Article
Language:English
Subjects:
Biomimetics
Carbon
Chemistry
Construction
Coupling
Diels-Alder reactions
Nitrogen atoms
Strategy
Synthesis
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Summary:(+)-Fastigiatine was assembled in six steps from ( )-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.
ISSN:2041-6520
2041-6539
DOI:10.1039/c5sc03262h