E74: (–)-Aplyviolene - chemie.unibas.chsparr/exercises/E74S.pdf · Sparr Group Seminar 30.05.2018...
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E74: (–)-Aplyviolene
[1] M. J. Schnermann, L. E. Overman, Angew. Chem. Int. Ed. 2012, 51, 9576 [2] M. J. Schnermann, L. E. Overman, J. Am. Chem. Soc. 2011, 133, 16425
Sparr Group Seminar30.05.2018
Alessandro Castrogiovanni
Me
MeMe
O
(+)-fenchone
1) NH2OH2) H2SO4, Δ
Me
Me
NCMe
3) DIBAL-H4) A, nBuLi5) HCl
TMSO PPh3A
Me
MeMe
HO6) I2, PPh37) AgNO2
Me
MeMe
O2N
8) PhNCO, Et3N, Δ9) Pd/C, RaNi,B(OH)3, H2
OH
H
OHMe
MeMe
10) TsOHO
HMeMe
Me11)
HMeMe
MgBr CuCN,
13) O3, Ph3P14) HF-py15) NaOCl2, NaH2PO42-methyl-2-butene
12) TMSCH2LiMe CO2H
HMeMe
Me 16) DCC, BO
ONPhth
N
O
O
OH
B
HH
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Sparr Group Seminar30.05.2018
Alessandro Castrogiovanni
HMeMe
Me O
ONPhth
17) C, D,Blue LED,[Ru(bpy)3](BF4)2iPr2EtN, CH2Cl2
O
ClH
MeO2C
TBSO
C
NH
EtO2C CO2Et
Me MeD
HMeMe
Me
H Cl
O
HTBSO
CO2Me
18) Me2CuCNLi2,TBSCl, HMPA
HMeMe
Me
H
HTBSO
CO2Me
OTBS
HMeMe
Me
H
HTBSO
OTBS
Me O
19) TiCl4,Zn, CH2Br220) (COOH)2
21) OsO4NMO22) Pb(OAc)4
HMeMe
Me CO2Me
H
HTBSO
Me O
O
HH H
HH23) TBAF24) DAST
HMeMe
Me O
HH
F
OMe
HMeMe
MeH OO
O
MeO2C
25) NaOH26) SnCl227) m-CPBA
Et N Et
SF FF
DAST
AcOH
(–)-aplyviolene
