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Named reactions

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Sarain A

"This manuscript is dedicated to Professor Nelson J. Leonard."

Chemical structure of Sarain_A
C32H50N2O3
Author Larry E. Overman
Publication year 2007
Synthesis type Total synthesis
Number of steps 51 (3 parts)
References

Browse hundreds of other total syntheses.

Part 1 of 3
Chemical structure
BH3.Me2S, NaBH4
THF
0 °C to RT, 26 h, 54%
Chemical structure
TBDPSCl, Imidazole
THF
0 °C to RT, 52 h, 82%
Chemical structure
H2, Pd/C
1 atm
EtOAc
RT, 24 h
Chemical structure + Chemical structure
CH2Cl2
RT, 24 h, 73% (2 steps)
Chemical structure

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Part 2 of 3
Chemical structure
TsNHBoc, DEAD, Ph3P
THF
0 °C to RT, 24 h, 88%

See the Mitsunobu Reaction
Chemical structure
  1. n-BuLi
  2. ClCO2Me
THF
-78 °C to RT, 92%
Chemical structure
H2, Lindlar Catalyst
1 atm
PhMe
RT, 3 h, 99%
Chemical structure

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Part 3 of 3
Chemical structure
+
Chemical structure
TMS2NLi
THF, DME
-78 °C, 4.5 h, 71%

See the Michael Addition
Chemical structure
DMSO
180 °C, 60 min, 69%
Chemical structure
AlMe3
PhMe
RT, 90 min, 91%
Chemical structure
  1. TMS2NLi
  2. AllylBr
THF, DMPU
-78 to -55 °C, 25 h, 92%
Chemical structure
HCl
THF, H2O
RT, 48 h, 98%
Chemical structure
Boc2O, DMAP
MeCN
RT, 15 h, 96%
Chemical structure
i-Bu2AlH
CH2Cl2
-78 °C, 25 min
Chemical structure
NaBH3CN
AcOH
RT, 12 h, 93% (2 steps)
Chemical structure
DMSO
130 °C, 4.5 h
Chemical structure
n-Bu4N+ F-, Ac2O
THF, Et3N
70 °C, 16 h

R = H or Ac (mixture)
Chemical structure
K2CO3
MeOH
RT, 12 h, 68% (3 steps)

R = H or Ac (mixture)
Chemical structure
i-Bu2AlH
CH2Cl2
-78 °C, 5 h, 87%
Chemical structure
NaOMe
THF
0 °C to RT, 4 h
Chemical structure
+
Chemical structure
Triphosgene, Et3N
CH2Cl2
0 °C, 45 min, 92% (2 steps)
Chemical structure
  1. O3, NaHCO3
  2. Me2S
CH2Cl2, MeOH
-78 °C to RT, 12 h, 92%
Chemical structure + Chemical structure
THF, Et2O
-78 to -10 °C, 80 min

See the Grignard Reaction
Chemical structure
COCl2, DMSO, Et3N
CH2Cl2
-78 °C to RT, 30 min, 83% (2 steps)

See the Swern Oxidation
Chemical structure
Ph3P+CH2O(CH2)2TMS Cl-, TMS2NK
THF
-78 °C to RT, 45 min

See the Wittig Reaction
Chemical structure
HF
MeCN, H2O
91% (2 steps)
Chemical structure
TIPSOTf, Et3N
CH2Cl2
-78 °C to RT, 12 h, 97%
Chemical structure
BCl3, 2,6-Di-tert-butyl-4-methylpyridine
CH2Cl2
RT, 15 h, 85%

See the Mannich Reaction
Chemical structure
TBSCl, Imidazole
MeCN
RT, 2 h
Chemical structure
NaBH4
MeOH
0 °C, 2 h
Chemical structure
TIPSOTf, Et3N
CH2Cl2
RT, 48 h, 75% (3 steps)
Chemical structure
Na, Naphtalene
DME, THF
-78 °C, 84%
Chemical structure + Chemical structure
NaBH3CN, AcOH
4 Å MS
MeCN
RT, 25 min, 94%
Chemical structure
Grubbs catalyst (1st gen.)
CH2Cl2
Reflux, 8 h

Selectivity : 66:33 E/Z
See the Olefin Metathesis
Chemical structure
H2, Pd/C
1 atm
EtOAc
RT, 6 h, 82% (2 steps)
Chemical structure
HCl
THF, H2O
RT, 6 h, 95%
Chemical structure
  1. TMS2NNa
  2. (4-MeOPh)CH2Cl
DMF
RT, 30 min, 89%
Chemical structure
TASF
DMA
100 °C, 60 min
Chemical structure
KOH
EtOH
90 °C, 12 h, 65% (2 steps)
Chemical structure + Chemical structure
PhH
80 °C, 3 h, 86%
Chemical structure
IBX
DMSO
RT, 105 min, 71%
Chemical structure + Chemical structure
THF
-15 °C, 60 min, 68%

Selectivity : 80:20 S/R
See the Grignard Reaction
Chemical structure
n-Bu4N+ F-
THF
RT, 105 min, 85%
Chemical structure
TESCl, Imidazole
DMF
0 °C, 15 min, 70%
Chemical structure
K2CO3
MeOH
0 °C to RT, 13 h, 92%
Chemical structure
Dess-Martin Periodinane, NaHCO3
CH2Cl2
0 °C, 90 min

See the Dess-Martin Oxidation
Chemical structure + Chemical structure
TMS2NNa
DME
-78 to 0 °C, 85 min, 76% (2 steps)

See the Wittig Reaction
Chemical structure
Pd(PPh3)4, LiCl
THF
RT, 7 d

See the Stille Coupling
Chemical structure
i-Bu2AlH
PhMe
-78 to 0 °C, 25 min, 64% (2 steps)
Chemical structure
Dess-Martin Periodinane, NaHCO3
CH2Cl2
0 °C, 20 min

See the Dess-Martin Oxidation
Chemical structure
Pyr.HF
CH2Cl2
0 °C, 90 min, 49% (2 steps)
Chemical structure

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