270
ORGANIC SYNTHESIS—1995
IV.H-7 Semmelhack, M.F. et al, JACS, 116, 7455; Mootoo, D.R. et al.,
JOC, 59, 7986.
Pd(OAc) 2
DMSO/AcOH
Ό Η
OH 70-80%
IV.H-8 Clark, J.S. and Whitlock, G.A., TL, 35, 6381
Cu(acac) 2
XX CH 2 C1 2 Me
v ** "O"
68%
intramolecular carbenoid insertion and ylide rearrangement
IV.H-9 Lee, E. et al., TL, 35, 129; Wu, S.-H. et al., CC, 2783.
H
CHO
1. Bu 3 SnH,AIBN
Ph-H, reflux
r T"
OAc
C0 2 Et
H
91%
IV.H-10 Motoyama, Y. and Mikami, K., CC, 1563; Yamamoto, H. et al.,
T, 50, 979 and SL, 439; Van de Weghe, P. and Collin, J., TL, 35, 2545;
Marko, I.E. et al., BSB, 102, 655 (1993); Olofson, R.A. et al., JOC, 59,
4117.
ph
v<*
i.
Lj~
Me
TMSO'
Ph
v
Λ
SQ 2 CF 3 T J
C ° 2
M e
toluene, -78 °C
CT^"
u
C0 2 M*
2.TFA
R'
69-86%, 80-94% de