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PESTAHIVIN synthesis

6synthesis methods
Hexanal, 6-hydroxy-4-methyl-, (4R)-

180908-43-4
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PESTAHIVIN

165754-55-2
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Yield:-

Steps:

Multi-step reaction with 13 steps
2: 94 percent / H2 / Pd/C
3: 90 percent / Dess-Martin reagent
4: 74 percent / CHCl3 / 16 h / -25 °C
5: Pb(OAc)4 / 0.17 h / 0 °C
6: aq. HCl / Heating
7: NaHCO3
8: 54 percent / NaHCO3, HOAt, EDCI / CH2Cl2; dimethylformamide / 32 h / 22 °C
9: HCO2H / 1 h / 22 °C
10: NaHCO3, HOAt, EDCI / CH2Cl2; dimethylformamide / 2 h / 0 °C
11: Ph3P, DIAD / toluene / 16 h / 22 °C
12: TFA, anisole / 1 h / 22 °C
13: 2,6-collidine, HATU / CH2Cl2 / 10 h / 25 °C

References:

Boger, Dale L.;Keim, Holger;Oberhauser, Berndt;Schreiner, Erwin P.;Foster, Carolyn A. [Journal of the American Chemical Society,1999,vol. 121,# 26,p. 6197 - 6205]