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Named reactions

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Decarestrictine D

Chemical structure of Decarestrictine_D
C10H16O5
Author Ronaldo A. Pilli
Publication year 1998
Synthesis type Total synthesis
Number of steps 15 (3 parts)
Reference

Browse hundreds of other total syntheses.

Part 1 of 3
Chemical structure
  1. NaH
  2. TBSCl
THF
0 °C, 91%
Chemical structure
(COCl)2, DMSO, Et3N
CH2Cl2
-78 °C to RT

See the Swern Oxidation
Chemical structure
(EtO)2P(O)CH2CO2Et, NaH
THF
0 °C, 70%

See the Horner-Wadsworth-Emmons Reaction
Chemical structure
AD-mix α, MsNH2
t-BuOH, H2O
94%

Selectivity : 96:04 er
See the Sharpless Asymmetric Dihydroxylation
Chemical structure
TBSCl, Imidazole
DMF
100%
Chemical structure
i-Bu2AlH
PhMe
-95 °C
Chemical structure
CrCl2, CHI3
THF
55 °C

See the Takai Reaction
Chemical structure
CrO3, H2SO4
Acetone, H2O
53% (2 steps)
Chemical structure

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Part 2 of 3
Chemical structure
LiAlH4
THF
15 °C to reflux, ON, 85%
Chemical structure
TBSCl
83%
Chemical structure

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Part 3 of 3
Chemical structure
+
Chemical structure
Reagent structure
Et3N, DMAP
THF, PhH
83%

See the Yamaguchi Esterification
Chemical structure
Pyr.HF
Pyr, THF
Chemical structure
Dess-Martin Periodinane
CH2Cl2, H2O

See the Dess-Martin Oxidation
Chemical structure
CrCl2, NiCl2
DMF
30% (3 steps)

See the Nozaki-Hiyama-Kishi Reaction
Chemical structure
n-Bu4N+ F-, HF
MeCN
80%
Chemical structure

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