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I<br />
1.Zn,THF,MeSi 3 Cl<br />
150 °C<br />
CO 2 Et<br />
Cr(CO) 3<br />
BF 4<br />
-<br />
2. CuCN, LiCl,<br />
-78°Cto0°C<br />
dioxane<br />
[6+2]<br />
<strong>tricyclic</strong><br />
1. LDA, THF-HMPA,<br />
MeI<br />
2. DIBAL, THF, 0 °C<br />
1. mCPBA, CH 2 Cl 2 ,0°C<br />
2. H 2 ,Pd(C),MeOH<br />
(separation of epimers)<br />
3. TsCl, py, 0 °C<br />
4. LiEt 3 BH,THF,0°C<br />
3. MeO 2 CNSO 2 NEt 3 (Burgess-reagent),<br />
PhH, 60 °C<br />
Tl(ONO 2 ) 3<br />
MeOH, rt<br />
1. H 3 O +<br />
2. NaBH 4 ,EtOH,0°C<br />
3. o-NO 2 C 6 H 4 SeCN, Bu 3 P, THF<br />
4. H 2 O 2 ,THF,rt
1.<br />
N<br />
O<br />
1. LDA, TMSCl, THF<br />
TBDMSOTf,<br />
CH 2 Cl 2 ,-78°C<br />
1. NaH, CS 2 then MeI<br />
O<br />
O<br />
2. Pd(OAc) 2 ,CH 3 CN<br />
O 2 atmosphere<br />
2.<br />
THF, -78 °C<br />
MgBr<br />
2. nBu 4 NF<br />
NH 2<br />
N<br />
Ph<br />
MeOH<br />
Ph<br />
1. nBu 3 SnH, AIBN,<br />
syringe pump, 20h<br />
2. TsOH, MeOH<br />
1. MeLi<br />
2. SOCl 2 ,py<br />
3. TsOH, CH 2 Cl 2<br />
H
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