tricyclic

I
1.Zn,THF,MeSi 3 Cl
150 °C
CO 2 Et
Cr(CO) 3
BF 4
-
2. CuCN, LiCl,
-78°Cto0°C
dioxane
[6+2]
tricyclic
1. LDA, THF-HMPA,
MeI
2. DIBAL, THF, 0 °C
1. mCPBA, CH 2 Cl 2 ,0°C
2. H 2 ,Pd(C),MeOH
(separation of epimers)
3. TsCl, py, 0 °C
4. LiEt 3 BH,THF,0°C
3. MeO 2 CNSO 2 NEt 3 (Burgess-reagent),
PhH, 60 °C
Tl(ONO 2 ) 3
MeOH, rt
1. H 3 O +
2. NaBH 4 ,EtOH,0°C
3. o-NO 2 C 6 H 4 SeCN, Bu 3 P, THF
4. H 2 O 2 ,THF,rt

1.
N
O
1. LDA, TMSCl, THF
TBDMSOTf,
CH 2 Cl 2 ,-78°C
1. NaH, CS 2 then MeI
O
O
2. Pd(OAc) 2 ,CH 3 CN
O 2 atmosphere
2.
THF, -78 °C
MgBr
2. nBu 4 NF
NH 2
N
Ph
MeOH
Ph
1. nBu 3 SnH, AIBN,
syringe pump, 20h
2. TsOH, MeOH
1. MeLi
2. SOCl 2 ,py
3. TsOH, CH 2 Cl 2
H