A practical entry to the crambescidin family of guanidine alkaloids. Enantioselective total syntheses of ptilomycalin A, crambescidin 657 and its methyl ester ( …

DS Coffey, AI McDonald, LE Overman…

Index: Coffey, D. Scott; McDonald, Andrew I.; Overman, Larry E.; Rabinowitz, Michael H.; Renhowe, Paul A. Journal of the American Chemical Society, 2000 , vol. 122, # 20 p. 4893 - 4903

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Citation Number: 63

Abstract

Among the most structurally remarkable guanidine natural products are the crambescidin/ ptilomycalin A family of marine alkaloids. The evolution of a practical strategy for preparing pharmacologically significant crambescidin/ptilomycalin A alkaloids that lack oxidation at C13 is described. The first total syntheses of crambescidin 800 (2), crambescidin 657 (6), and neofolitispate 2 (7) are reported in full detail. The central strategic step in these ...