Biomedical Engineering Reference
In-Depth Information
SCHEME 7.25
Synthesis of a library containing 242 compounds based on 18 discrete nat-
ural product-like scaffolds. Reagents and conditions: (i) R
1
CHO, LiBr, DBU, MeCN; (ii)
(
R
)-QUINAP, AgOAc, DIEA, THF,
−
78
◦
C
→
rt; (iii) AD-mix, (DHQD)2-PHAL, THF/H
2
O
(1 : 1); (iv) chiral bis(oxazoline), Cu(OTf)
2
, DCM, C
5
H
6
; (v) R
2
COCl, DMAP, pyridine, DCM;
(vi) R
3
CHO, BH
3
·
pyridine, MeOH; (vii) SOCl
2
, pyridine, DCM, 40
◦
C; (viii) NaN
3
,DMF,
100
◦
C; (ix) DMAD, toluene, 65
◦
C; (x) R
4
Br, Ag
2
O, DCM, 40
◦
C; (xi) (R
5
)
2
CO, TsOH, DMF,
65
◦
C; (xii) R
6
CHO, TsOH, DMF, 65
◦
C; (xiii)
m
CPBA, DCM; (xiv) MeOH, 65
◦
C; (xv)
CH
2
=
CH
2
, toluene, 120
◦
C; (xvi) OsO
4
, NMO, acetone/H
2
O
(10 : 1); (xvii) RNH
2
,Me
2
AlCl, toluene, 120
◦
C; (xviii) NaH, R
11
X, DMF/THF; (xix) Grubbs
II, CH
2
=
CHCOOBn, Grubbs II, CH
2
=
CH
2
, toluene, 120
◦
C; (xx) NaIO
4
, THF/H
2
O (1 : 1); (xxi) R
7
NH
2
, NaBH(OAc)
3
,
DCM; (xxii) R
8a
R
8b
NH, NaBH(OAc)
3
, DCM; (xxiii) R
9
CHO, TsOH, DMF, 65
◦
C; (xxiv)
(R
10
)
2
CO, TsOH, DMF, 65
◦
C.
