Total synthesis of the marine toxin polycavernoside A via selective macrolactonization of a trihydroxy carboxylic acid

…, PA Nagornyy, LA Robarge, DJ Wardrop

Index: White; Blakemore; Browder; Hong; Lincoln; Nagornyy; Robarge; Wardrop Journal of the American Chemical Society, 2001 , vol. 123, # 35 p. 8593 - 8595

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Citation Number: 80

Abstract

Naturally occurring macrolactones (macrolides) are found in a wide variety of ring sizes, yet little is known of the propensity of their precursor seco acids for forming a particular ring size when more than one macrocyclization pathway is available. 1 There does, nevertheless, appear to be a preponderance of macrolides with 14-and 16-membered rings, reflecting a bias by the synthase which fabricates these systems toward rings of this size. Our plan for ...