Synthesis of Decarestrictine D

Structure of Decarestrictine D

C10H16O5

Principal investigatorRonaldo A. Pilli
Publication year1998
Synthesis typeTotal
Number of steps 15 (3 parts)
References
Part 1 of 3
intermediate structure
  1. NaH
  2. TBSCl
THF
0 °C, , 91%
intermediate structure
(COCl)2, DMSO, Et3N
CH2Cl2
-78 °C to RT
See the Swern Oxidation
intermediate structure
NaH, (EtO)2P(O)CH2CO2Et
THF
0 °C, , 70%
intermediate structure
MsNH2, AD-mix A
H2O, t-BuOH
94%
intermediate structure
Imidazole, TBSCl
DMF
100%
intermediate structure
i-Bu2AlH
PhMe
-95 °C
intermediate structure
CrCl2, CHI3
THF
55 °C
See the Takai Reaction
intermediate structure
CrO3, H2SO4
Acetone, H2O
53% (2 steps)
intermediate structure
Part 2 of 3
intermediate structure
LiAlH4
THF
15 °C to reflux, ON, 85%
intermediate structure
TBSCl
83%
intermediate structure
Part 3 of 3
intermediate structure + intermediate structure
DMAP, Et3N
PhH, THF
83%
intermediate structure
Pyr.HF
Pyr, THF
intermediate structure
Dess-Martin Periodinane
CH2Cl2, H2O
intermediate structure
CrCl2, NiCl2
DMF
30% (3 steps)
intermediate structure
HF, n-Bu4N+ F-
MeCN
80%
intermediate structure