140531_kaiTM.cdx

O
N2
EtO
MeO2C
O
O
EtO
(S,S)-iPr-BOX
BF3·OEt2
allyltrimethylsilane
CO2Me
Me3Si
OH
O
MeOH
Et3N
O
OH
MeOH
I2, PPh3
imidazole
ZnI
O
Br
CO2tBu
H
H
O
Ring Closing
Metathesis
CO2tBu
O
O
H
H
Se
O
O
CO2tBu
H
SeO2
O
O
H
Riley Selenium
Dioxide Oxidation
O
O
Se O
HO
H
O
O
CO2tBu
H
OAc
Me
CO2tBu MeCu(CN)Li2
H
CO2tBu DMAP (cat.)
Ac2O
O
H
O
H
OH
H
O
OH
Se
O
H
H
CO2tBu
Grubbs II (cat.)
O
CuCN·2LiCl
O
CO2tBu
O
NaBH4
O
active Zn
O
Appel Reaction
Cu(CN)ZnI
O
O
I
O
O
OEt
OHC
Retroaldol
Reaction
CO2Me
CHO
CO2Me
OEt
OH
CO2Et
Hosomi-Sakurai Allylation
OH
O
O
O
SiMe3
O
O
O
O
CO2Et
O
N
N
MeO2C
BF3·OEt2
O
O3;
Me2S
O
O
CO2Et
Cu(OTf)2 (cat.)
(S,S)-iPr-BOX (cat.)
PhNHNH2 (cat.)
CuLn
O
H
SN2'
H
O
O
CO2tBu
H
Li
TrO
TBDPSCl
TrO
O
p-TsOH•H2O
TrO
imidazole
OH
HO
OTBDPS
OTBDPS
O
O
O
I OAc
AcO OAc
(o-MeC6H4)2P(O)CHMeCO2Et
Ando's reagent
O
OTBDPS
Dess-Martin oxidation
OEt
LAH
HWE reaction
OTBDPS
CBr4, PPh3
OH
Br
OH
B
OH
Appel reaction
OTBDPS
OTBDPS
Pd(dba)2
K3PO4
A
OTBDPS
Suzuki-Miyaura coupling
Bu3SnH, AIBN
TBAF
SnBu3
Bu3Sn
R
OTBDPS
SnBu3
OTBDPS
Bu3Sn H
OTBDPS
OTBDPS
OsO4, NMO
PMBO(=NH)CCl3
CSA
MgBr
OTBDPS
DDQ
OTBDPS
O
R
OH
OTBDPS
OTBDPS
NaIO4
OH
OPMB OH
OPMB
OH
SnBu3
OsO4, NMO
OPMB
OTBDPS
O
; NaIO4
H
PMBO
OH
O
O
PMP
O
O
O
PMP
BnO
OTBDPS
OTBDPS
BnO
NiCl2, CrCl2
O
O
O
PMP
O
Ni(0), Cr(III)
I
O
OH
Nozaki-Hiyama-Kishi reaction PMP
HO
BnO
OTBDPS
Me3O BF4
OTBDPS
Li
Meerwein's reagent
O
O
O
OMe
OMe
PMP
PMP
I
O
TEMPO
O
OTBDPS
CHI3, CrCl2
I
OTBDPS
TBAF
OH
PhI(OAc)2
O
O
OMe
O
Takai olefination reaction
PMP
O
OMe
O
PMP
PMP
I
TEMPO
I
O
NaClO2, NaH2PO4
O
OH
PhI(OAc)2
O
O
PMP
OMe
O
O
O
PMP
OMe
OMe

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