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Regio- and Stereoselective Functionalization of Linear Dicarboxylic Acid Derivatives. A Sequential Aldol-Lactonization Strategy for the Synthesis of (-)-Roccellaric Acid, (-)-Protolichesterinic Acid, and (-)-Methylenolactocin
31 December 2000 (online)
A regio- and stereoselective functionalization methodology of linear dicarboxylic acids has been developed and applied in the synthesis of paraconic acid natural products. Using this strategy, (-)-roccellaric acid 1a was prepared in 25% overall yield. The formal total synthesis of (-)-protolichesterinic acid 1b and (-)-methylenolactocin 1c has been accomplished starting from a differentially functionalized succinate 5.
Butyrolactones - Roccellaric acid - Protolichesterinic acid - Methylenolactocin - Tandem reactions - Aldol reaction