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Synlett 1996; 1996(4): 343-345
DOI: 10.1055/s-1996-5427
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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

Mukund P. Sibi* , Prasad K. Deshpande, Anthony J. La Loggia
  • *Department of Chemistry, North Dakota State University, Fargo, ND 58105-5516, USA, Fax: 701-231-8831; Internet: Sibi@plains.nodak.edu
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Publikationsdatum:
31. Dezember 2000 (online)

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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

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