pentane, 20 °C
93%THF-EtOH (5:1) 20 °C, 69%
1) m -CPBA (1.1 eq) CH 2Cl 2, rt, 3 hr 82%
2) NaOH, MeOH rt, 5 min, 71%3) TFA, CH 2Cl 2 rt, 15 hr, 52%
(OC)5W
OEt
Ph
O
N
Me
H
Ph
[(COD)RhCl]2
乔伊斯N
Ph
Ph
O OEt Me
N
N H
MeO 2C Cl
MeO
N
CHO N
H CO 2Me
HO
NH 2
O CN
O
N CH 3(CH 2)14
氨基酸合成CH 3OCH 3
O N CH 3(CH 2)14
CH 3OTBS
1
5
2
3
4
Tungsten-carbene complex
HCOOH
paraformaldehyde CH 3CN reflux, 12 hr
85%
TBSOTf (2.1 eq)collidine (4.2 eq)
CH 2Cl 2rt, 3 hr 61%
S
Li
Cl
1)2) HgCl 2, H 2O
N
1
5
2
3
4
Me
MgBr Cp 2TiCl 2;MeMgBr,
OTIPS ;
Br 2 (2 eq)
1) BnNH 2, Pd 2(dba)3, P(o -tolyl) NaO t-Bu黎曼
2) Pd-C, HCO 2NH 4, MeOH reflux
N H
Me
OTIPS
3
O
Me
Pentacyclic compound
O
Me
COCN 2CO 2t -Bu
OBn
1) NaBH 4, MeOH 0 °C
2) NaH, BnBr, DMF 0-23 °C
3) DIBAL, CH 2Cl 2 –10 °C
4) Tf 2O, 2,6-lutidine CH 2Cl 2, –78 °C
MeO 2C
PPh 3
O
COPh NBS, TMSN 3
heat in toluene
N
O
Ph Br
MeO 2C
CO 2Et
TBSO
Ti(O i -Pr)42 i -PrMgCl Et 2O
1) FeCl 32) AcONa
O
TBSO
C 12H 24O 2Si
( racemic )
O Cu N N O t -Bu t -Bu
toluene reflux
N CO 2Me
Cl cat. Cu(bpy)Cl ClCH 2CH 2Cl reflux, 48 h
66%
1) 30% aq HCl reflux, 18 h朱时华
2) pH 13
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