Investigation of methods for seven-membered ring synthesis: a practical synthesis of 4-oxo-5, 6, 7, 8-tetrahydro-4H-cyclohepta [b] furan-3-carboxylic acid

…, TW Makowski, R McDermott, BJ Sitter…

Index: Ragan, John A.; Murry, Jerry A.; Castaldi, Michael J.; Conrad, Alyson K.; Jones, Brian P.; Bryan, Li; Makowski, Teresa W.; McDermott, Ruth; Sitter, Barb J.; White, Timothy D.; Young, Gregory R. Organic Process Research and Development, 2001 , vol. 5, # 5 p. 498 - 507

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Citation Number: 24

Abstract

Several synthetic routes to 4-oxo-5, 6, 7, 8-tetrahydro-4H-cyclohepta [b] furan-3-carboxylic acid (1) are described, and the scale-up issues with each route are discussed. Seven- membered ring formation is a key issue with these syntheses, and several strategies are presented, including preparation from cycloheptane-1, 3-dione, ring-expansion routes, Dieckmann cyclization, acetylene-furan [4+ 2] cycloaddition, and Friedel-Crafts cyclization. ...