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Named reactions

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Fredericamycin A

Chemical structure of Fredericamycin_A
C30H21NO9
Author Dale L. Boger
Publication year 1995
Synthesis type Total synthesis
Number of steps 27 (3 parts)
References

Browse hundreds of other total syntheses.

Part 1 of 3
Chemical structure
MeOCH2Cl, NaH, n-Bu4N+ I-
DMF
0 °C to RT, 24 h, 91%
Chemical structure
mCPBA
CH2Cl2
RT, 16 h

See the Baeyer-Villiger Oxidation
Chemical structure
KOH
MeOH, H2O
RT, 12 h, 85% (2 steps)
Chemical structure
MeOCH2Cl, NaH, n-Bu4N+ I-
DMF
RT, 72 h, 71%
Chemical structure
n-BuLi, Cr(CO)6
Et2O
-78 °C to RT, 2.5 h
Chemical structure
Me3O+ BF4-
CH2Cl2
0 °C to RT, 90 min, 78% (2 steps)
Chemical structure

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Part 2 of 3
Chemical structure
MeSOCl, Et3N
CCl4
0 °C, 10 min
Chemical structure + Chemical structure
CH2Cl2
RT, 20 h, 47% (2 steps)

See the Diels-Alder Reaction
95 % yield based on the alkene.
Chemical structure
DBU
THF
70 °C, 40 h, 81-91%
Chemical structure + Chemical structure
i-Pr2NLi
THF
-78 °C to RT, 3 h, 64-85%

See the Michael Addition
See the Dieckmann Condensation
Chemical structure
DDQ
CH2Cl2
RT, 10 min, 87%
Chemical structure
BnBr, K2CO3, n-Bu4N+ I-
DMF
RT, 6 h, 93%

See the Williamson Ether Synthesis
Chemical structure
TosMIC, KOt-Bu
CH2Cl2, EtOH
0 °C to 10 °C, 5 h, 73%

See the Van Leusen Reaction
Chemical structure
i-Bu2AlH
THF
-78 °C, 3 h, 97%
Chemical structure
(COCl)2, DMSO, Et3N
CH2Cl2
-70 °C to RT, 40 min, 99%

See the Swern Oxidation
Chemical structure + Chemical structure
n-BuLi
THF
-78 °C to RT, ON, 89%

Selectivity : 07:41:12:40
See the Wittig Reaction
Ratio of the cis-cis, cis-trans, trans-cis and trans-trans isomers, respectively.
Chemical structure
I2
CHCl3
RT, 4-5 d

Selectivity : 85:15
Chemical structure
i-Bu2AlH
PhMe
-30 °C, 60 min, 69% (2 steps)
Chemical structure + Chemical structure
n-BuLi
THF
-78 to 0 °C, 2.5 h

Mixture of diastereoisomers.
Chemical structure
TBSCl, Imidazole
DMF
RT, 22 h, 54% (2 steps)
Chemical structure

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Part 3 of 3
Chemical structure
+
Chemical structure
Ac2O
Heptane
50 °C, 47 h, 35%

See the Wulff-Dötz Reaction
Chemical structure
BnBr, K2CO3, n-Bu4N+ I-
DMF
RT, 53 h, 50-57%

See the Williamson Ether Synthesis
Chemical structure
n-Bu4N+ F-
THF
RT to 50 °C, 10.5 h
Chemical structure
(CF3CO)2O, DMSO, DBU
CH2Cl2
-78 °C to RT, 21 h

See the Swern Oxidation
See the Aldol Addition
Chemical structure
(CF3CO)2O, DMSO, Et3N
CH2Cl2
-78 °C to RT, 50 min, 57-68% (3 steps)

See the Swern Oxidation
Chemical structure
  1. BBr3
  2. O2, HCl, H2O
CH2Cl2
-78 °C to RT, 4 h

Partial deprotection of the imide.
Chemical structure
TsOH, NaBr
MeOH
70 °C, 12 h, 85% (2 steps)
Chemical structure

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