Synthesis of Defucogilvocarcin V

Structure of Defucogilvocarcin V

C21H16O5

Principal investigator	Victor Snieckus
Publication year	1997
Synthesis type	Total
Number of steps	11 (3 parts)
References	Tetrahedron Lett. 1997, 47, 8149.

Part 1 of 3

intermediate structure

Zn, ClCONEt2

CHCl3, Pyr

Reflux, 2 h, 70%

intermediate structure

K2CO3, MeI

Acetone

Reflux, 84%

See the Williamson Ether Synthesis

intermediate structure

(CH2NMe2)2 , s-BuLi
I2

THF

-78 °C to RT, 6.5 h, 94%

intermediate structure

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Part 2 of 3

intermediate structure

NaH
MeOCH2Cl

DMF

0 °C to RT, 2.5 h, 91%

intermediate structure

n-BuLi
B(OMe)3
H2O , HCl

THF

-78 °C to RT, 72%

intermediate structure

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Part 3 of 3

intermediate structure

+

intermediate structure

Ba(OH)2, Pd(PPh3)4

DME, H2O

Reflux, 3 h, 99%

See the Suzuki Coupling

intermediate structure

LDA

THF

Reflux, 3 h

intermediate structure

AcOH

H2O

Reflux, 70 min, 70% (2 steps)

intermediate structure

Tf2O, Et3N

CH2Cl2

-78 °C, 60 min, 81%

intermediate structure

(2-Furyl)3P, VinylSnBu3, Pd2(dba)3, LiCl

NMP

RT, 1 h, 69%

See the Stille Coupling

intermediate structure

BCl3

CH2Cl2

0 °C, 15 min, 95%

intermediate structure

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