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A concise and efficient approach to the stereoselective total synthesis of (+)-secosyrin 1 and (+)-syributin 1

Authors : Perali Ramu Sridhar*and Boddu Umamaheswara Rao


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Abstract

A concise and stereoselective approach for the total synthesis of (+)-secosyrin 1 and (+)-syributin 1, metabolites of Pseudomonas syringae, is reported. The key synthetic step in this approach is a highly stereoselective construction of spiro center, through a one-pot dehydrohalogenation, intramolecular hetero-Michael addition (IHMA) and ester hydrolysis of halohydrins derived by the ring opening of 1,2-cyclopropanecarboxylated xylal derivative.

Keyword

Carbohydrates, spiro-sugars, Michael addition, secondary metabolites, plant defense