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. 2004 Jun 1;101(33):11955–11959. doi: 10.1073/pnas.0401247101

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Copyright © 2004, The National Academy of Sciences

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Scheme 6. — Synthesis of aldehyde 14. a, TBS trifluoromethanesulfonate, 4 Å MS, CH₂Cl₂, 23°C, 15 min, 84%; b, tetrabutylammonium fluoride, THF, 0°C → 23°C, 1.5 h, 84%; c, Dess–Martin periodinane, pyridine, wet CH₂Cl₂, 0°C → 23°C, 2.5 h, 92%; d, CBr₄, Ph₃P, CH₂Cl₂, 0°C → 23°C, 30 min, 94%; e, O₃, 4:1 CH₂Cl₂/MeOH, KHCO₃, -78°C → 23°C, 3 h; f, Ph₃PCHCO₂Me, CH₂Cl₂, 23°C, 12 h, 82% from 19, ds = 95:5; g, diisobutylaluminum hydride, CH₂Cl₂, -78°C → 0°C, 1.25 h, 89%; h, SO₃·pyridine, DMSO, i-Pr₂NEt, CH₂Cl₂, 0°C, 20 min.

Inline graphic — Synthesis of aldehyde 14. a, TBS trifluoromethanesulfonate, 4 Å MS, CH₂Cl₂, 23°C, 15 min, 84%; b, tetrabutylammonium fluoride, THF, 0°C → 23°C, 1.5 h, 84%; c, Dess–Martin periodinane, pyridine, wet CH₂Cl₂, 0°C → 23°C, 2.5 h, 92%; d, CBr₄, Ph₃P, CH₂Cl₂, 0°C → 23°C, 30 min, 94%; e, O₃, 4:1 CH₂Cl₂/MeOH, KHCO₃, -78°C → 23°C, 3 h; f, Ph₃PCHCO₂Me, CH₂Cl₂, 23°C, 12 h, 82% from 19, ds = 95:5; g, diisobutylaluminum hydride, CH₂Cl₂, -78°C → 0°C, 1.25 h, 89%; h, SO₃·pyridine, DMSO, i-Pr₂NEt, CH₂Cl₂, 0°C, 20 min.