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Synfacts 2012; 8(7): 0695
DOI: 10.1055/s-0032-1289843
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (+)-Merobatzelladine B

Contributor(s):
Steven V. Ley
,
Sean Newton
Babij NR, Wolfe JP * University of Michigan, Ann Arbor, USA
Asymmetric Total Synthesis of (+)-Merobatzelladine B.

Angew. Chem. Int. Ed. 2012;
51: 4128-4130
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Further Information

Publication History

Publication Date:
19 June 2012 (online)

 
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Key words

asymmetric Mannich reaction - palladium-catalyzed carboamination - intramolecular Mitsunobu reaction

Significance

Merobatzelladine B was isolated in 2009 from the marine sponge Monanchora sp. by Matsunaga and co-workers. It exhibits moderate antimicrobial activity and inhibitory effects against a strain of Plasmodium falciparum. It possesses a fused tricyclic guanidine core and two n-pentyl chains that are positioned anti to one another.


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Comment

This synthesis utilizes iterative stereo- and regioselective palladium-catalyzed carboamination reactions to build two of the three fused heterocycles in good yield and excellent diaste­reoselectivity. The selectivity of the second carboamination step is attributed to the preferred boat-like transition structure K, which minimizes steric hindrance with the previously formed pyrrolidine ring and the metal center.


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