Synthesis of Tirandamycin B

Structure of Tirandamycin B

C22H27NO8

Principal investigator	Philip DeShong
Publication year	1991
Synthesis type	Total
Number of steps	18 (linear)
References	J. Am. Chem. Soc. 1991, 113, 8791.

Part 1 of 1

intermediate structure

+

intermediate structure

LiAlH4, 																	
																						CrCl3

																	THF															

								0 °C to RT, 								5 h, 								30%
							
								See the Nozaki-Hiyama-Kishi Reaction
							
								"Also isolated was the C2-epimer (47 % yield)."

intermediate structure

Imidazole, TBSCl

DMF

RT, 5 d, 82%

intermediate structure

O3

CH2Cl2

-78 °C

intermediate structure

AcOH, Zn

Et2O, H2O

RT, 2 h, 95% (2 steps)

intermediate structure

+

intermediate structure

t-BuLi, (CH2NMe2)2

Et2O

-78 to 0 °C, 4 h, 42%

"Also isolated was the C1-epimer (42 % yield)."

intermediate structure

mCPBA

CH2Cl2

RT, 3 h, 89%

See the Achmatowicz Reaction

intermediate structure

H2SiF6, HF

H2O, MeCN

RT, 20 min, 35%

intermediate structure

CeCl3, NaBH4

MeOH

RT, 5 min, 99%

See the Luche Reduction

intermediate structure

mCPBA, Na3PO4

CH2Cl2, H2O

RT, 24 h, 73%

See the Prilezhaev Reaction

intermediate structure

Li.DTBBP

THF

-78 °C, 3 h, 95%

intermediate structure

H2Cr2O7.2Pyr

CH2Cl2

RT, 7 h, 85%

intermediate structure

+

intermediate structure

LiAlH4, CrCl3

THF

0 °C to RT, 3 h, 81%

See the Nozaki-Hiyama-Kishi Reaction

intermediate structure

OsO4, NaIO4

Dioxane , H2O, t-BuOH

RT, 7 h, 85%

See the Lemieux-Johnson Oxidation

intermediate structure

TsOH

PhH

Reflux, 2 h, 75%

intermediate structure

+

intermediate structure

KOt-Bu

THF

0 °C, 18 h, 72%

See the Horner-Wadsworth-Emmons Reaction

intermediate structure

CF3CO2H

RT, 5 min, 98%

intermediate structure

n-Bu4N+ F-

THF

RT, 21 h

intermediate structure

PhMe

Reflux, 91% (2 steps)

intermediate structure

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