Synthesis of Tirandamycin B

C22H27NO8
Principal investigator | Philip DeShong |
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Publication year | 1991 |
Synthesis type | Total |
Number of steps | 18 (linear) |
References |
Part 1 of 1
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LiAlH4,
CrCl3
THF
0 °C to RT, 5 h, 30%
See the Nozaki-Hiyama-Kishi Reaction
"Also isolated was the C2-epimer (47 % yield)."

Imidazole,
TBSCl
DMF
RT, 5 d, 82%

O3
CH2Cl2
-78 °C

AcOH,
Zn
Et2O, H2O
RT, 2 h, 95% (2 steps)


t-BuLi,
(CH2NMe2)2
Et2O
-78 to 0 °C, 4 h, 42%
"Also isolated was the C1-epimer (42 % yield)."


H2SiF6,
HF
H2O, MeCN
RT, 20 min, 35%



Li.DTBBP
THF
-78 °C, 3 h, 95%

H2Cr2O7.2Pyr
CH2Cl2
RT, 7 h, 85%




TsOH
PhH
Reflux, 2 h, 75%



CF3CO2H
RT, 5 min, 98%

n-Bu4N+ F-
THF
RT, 21 h

PhMe
Reflux, 91% (2 steps)
