Industrial Biotransformations

Lipase
Pseudomonas fluorescens
O
O
HO H
O
H
HO H
O
(+)-1
H
(+)-1
1 = hydroxylactone
2 = brefeldin A
Fig. 3.1.1.3 – 3
6) Literature
1) LiAlH 4
2) NaIO
3) NaBH4
4) Ph3CCl
TBDMSO
HO
H
H
1) Ph3P, ClCH 2COOH, DEAD
2) thiourea, EtOH
1) LiAlH4
2) NaIO
3) NaBH4
4) TBDMSO
5) PCC
6) H 2O2, NaOH
7) Al-Hg
H
H
O
OH
TBDMSO H
EC 3.1.1.3
● Evans, C.T., Roberts, S.M., Shoberu, K.A., Sutherland, A.G. (1992) Potential use of carbocylic
nucleosides for the treatment of AIDS: Chemo-enzymatic syntheses of the enantiomers of carbovir;
J. Chem. Soc. Perkin Trans. 1, 589–592
● MacKeith, R.A., McCague, R., Olivo, H.F., Palmer, C.F., Roberts, S.M. (1993) Conversion of (–
)-4-hydroxy-2-oxabicyclo[3.3.0]oct-7-en-3-one into the anti-HIV agent Carbovir, J. Chem. Soc.
Perkin Trans. 1 1, 313–314
● MacKeith, R.A., McCague, R., Olivo, H.F., Roberts, S.M., Taylor, S.J.C., Xiong, H. (1994)
Enzyme-catalysed kinetic resolution of 4-endo-hydroxy-2-oxabicyclo[3.3.0]oct-7-en-3-one and
employment of the pure enantiomers for the synthesis of anti-viral and hypocholesteremic
agents, Bioorg. Med. Chem. 2, 387–394
● Taylor, S.J.C., McCague, R. (1997) Resolution of a versatile hydroxylactone synthon 4-endohydroxy-2-oxabicyclo[3.3.0]oct-7-en-3-one
by lipase deesterification, in: Chirality In Industry II
(Collins, A. N., Sheldrake, G. N. and Crosby, J., eds.), pp. 190–193, John Wiley & Sons, New
York
O
O O
HO
OH
1) MCPBA
2) AcOH
H
H
OMEM
OH
2
OH
OTBDMS
O O
COOMe
O
O
293