Total Synthesis of Polycavernoside A, A Lethal Toxin of the Red Alga Polycavernosa t sudai

…, PA Nagornyy, LA Robarge, DJ Wardrop…

Index: Blakemore, Paul R.; Browder, Cindy C.; Hong, Jian; Lincoln, Christopher M.; Nagornyy, Pavel A.; Robarge, Lonnie A.; Wardrop, Duncan J.; White, James D. Journal of Organic Chemistry, 2005 , vol. 70, # 14 p. 5449 - 5460

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Citation Number: 58

Abstract

Two approaches to the synthesis of the aglycon 120 of polycavernoside A (1) were developed, only one of which was completed. The successful “second-generation” route assembled the aglycon seco acids 102 and 106 via Nozaki-Hiyama-Kishi coupling of aldehyde 70, prepared from methyl (S)-3-hydroxy-2-methylpropionate (72) and (S)- pantolactone (73), with vinyl bromide 71. The latter was obtained from a sequence which ...