Biomedical Engineering Reference
In-Depth Information
(a)
SCHEME 1.6
Synthesis of structurally diverse bicyclic “fragments” by Hung et al.
[58] using the build/couple/pair approach. (a) (
S
)-Allylglycine methyl ester, 1-ethyl-3-(3-
dimethylaminopropane), ethyl(hydroxyimino)cyanoacetate, Et
3
N, CH
2
Cl
2
; NaH, MeI, DMF;
(b) Grubbs II, CH
2
Cl
2
reflux; TFA; (c) allylamine, 1-ethyl-3-(3-dimethylaminopropane),
ethyl(hydroxyimino)cyanoacetate Et
3
N, CH
2
Cl
2
; NaH, MeI, DMF; (d) Grubbs II, toluene,
TFA; (e) allyl isocyanate, CH
2
Cl
2
; (f) NaH, DMF; (g) 2-chlorosulfonyl chloride, Et
3
N,
CH
2
Cl
2
; (h) Grubbs II, CH
2
Cl
2
, reflux; (i) prop-2-ene-1-sulfonyl chloride, Et
3
N, CH
2
Cl
2
;
(j) Grubbs II, CH
2
Cl
2
, reflux; (k) LiAlH
4
, THF,
t
-butyldimethylsilylchloride, Et
3
N, CH
2
Cl
2
;
2-chlorosulfonyl chloride, Et
3
N, CH
2
Cl
2
; (l) tetrabutylammonium fluoride, THF; (m) (
S
)-
N
-Boc-allylglycine, 1-ethyl-3-(3-dimethylaminopropane), ethyl(hydroxyimino)cyanoacetate
Et
3
N, CH
2
Cl
2
; (n) Grubbs II, CH
2
Cl
2
,TFA.
