Synthesis of Aplysistatin

C15H21BrO3

Principal investigator	Elias A. Couladouros
Publication year	2005
Synthesis type	Total
Number of steps	19 (3 parts)
References	Chem. Eur. J. 2005, 10, 3822.

Part 1 of 3

i-Bu2AlH

CH2Cl2

-78 °C, 30 min

H2SO4, CrO3

Acetone

-20 °C, 7 min, 60 % (2 steps)

(CF3CO)2O

t-BuOH

RT, 60 min, 85%

(DHQD)2PHAL, 																	
																						K2OsO2(OH)4, 																	
																						K3Fe(CN)6, 																	
																						MsNH2, 																	
																						K2CO3

																	H2O, 																	t-BuOH															

								0 °C, 								15h, 								61%
							
								See the Sharpless Asymmetric Dihydroxylation
							
								"97% ee"

Ts2O

Pyr

0 °C, 60 min, 86%

DBU

DMF

RT, 15 min, 87%

LiBr, Pyr.TsOH

NMP

RT, 60 min, 85%

SnCl4

MeNO2

0 °C, 40 min, 60%

i-Bu2AlH

CH2Cl2

-78 °C, 40 min, 97%

Ph3P+CH3 Br-, TMS2NNa

THF

0 °C to RT, 13 h, 60%

See the Wittig Reaction

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Part 2 of 3

Pd2(dba)3

CH2Cl2

RT, 3 h, 60%

See the Stille Coupling

t-BuOOH, 																	
																						Ti(Oi-Pr)4, 																	
																						(+)-DIPT4A MS

																	CH2Cl2															

								-20 °C, 								12.5 h, 								80%
							
								See the Sharpless Epoxidation
							
								"95% ee"