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J Am Chem Soc. 2010 Jul 21;132(28):9594-5. doi: 10.1021/ja104575h.

Total synthesis of (+)-fastigiatine.

Author information

1
Department of Chemistry & Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA.

Abstract

The first total synthesis of the Lycopodium alkaloid (+)-fastigiatine has been accomplished in 15 steps and 30% overall yield from known compounds. Noteworthy transformations include a convergent fragment coupling via a nucleophilic cyclopropane opening, a highly diastereoselective formal [3 + 3]-cycloaddition, and a transannular Mannich reaction to construct the core of the natural product.

PMID:
20568766
DOI:
10.1021/ja104575h
[Indexed for MEDLINE]

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