A formal convergent synthesis of (+)- trans-solamin

A modular formal synthesis of (+)-solamin is disclosed. A formal convergent synthesis of solamin is disclosed. The synthetic strategy exploits the potential of the sulfinyl group as an auxiliary, nucleophile and in C–C bond formation. The synthetic route can be adapted to the synthesis of stereoisom...

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Bibliographic Details
Published in:Tetrahedron letters 2008-03, Vol.49 (10), p.1601-1604
Main Authors: Raghavan, Sadagopan, Ganapathy Subramanian, S., Tony, K.A.
Format: Article
Language:English
Subjects:
Bromohydrin
NBS
Pummerer ene reaction
Sulfoxide
trans-Solamin
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Summary:A modular formal synthesis of (+)-solamin is disclosed. A formal convergent synthesis of solamin is disclosed. The synthetic strategy exploits the potential of the sulfinyl group as an auxiliary, nucleophile and in C–C bond formation. The synthetic route can be adapted to the synthesis of stereoisomers of solamin, analogs with variable carbon side chains, and other members of mono-THF acetogenins.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2008.01.046