Improved Synthesis of the C₈-C₂₃ Segment of Aplysiatoxins via Asymmetric Dihydroxylation of the Chiral Homoallylic Alcohol

Abstract

Important intermediate 2 of the segment (3) possessing four sequential asymmetric centers (C₉-C₁₂) of aplysiatoxins was synthesized via dihydroxylation of 5 in only 7 steps from methyl (S)-3-hydroxy-2-methylpropionate. Another promising compound (10a) was also synthesized in only 6 steps via asymmetric dihydroxylation of chiral homoallylic alcohol 4 as the key step.

• aplysiatoxin
• tumor promoter
• protein kinase C
• crotylboration
• asymmetric dihydroxylation