Chemistry Reference
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LiAlH 4 /BuOH, THF
O
Ph
O
Ph
+
O
O
O
O
O
O
OH
OH
(+)-inophyllum B (+)-inophyllum P
2, 91%
( 3 )
( 4 )
9%
Scheme 8-8
(Continued )
OH
O
O
2 steps
2 steps
75%
HO
OH
HO
O
O
O
O
O
O
39
40
O
O
(-)-quinine
MgI 2
+
O
O
O
O
O
O
PhCl
K 2 CO 3 , PhH
cis -(+)-41
O
O
trans -(-)- 41
cis -(+)- 41
39% ee 98% ee
21% 67%
higher enantioselectivity lower enantioselectivity
OH
OH
+
O
O
O
O
O
O
O
O
cis - 42
trans -( 42 ) major product
diastereomeric mixture
without separation
Scheme 8-9
 
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