LETTER
An Approach to b-Substituted g-Butyrolactones
1943
O
O
References
ClMg
(16)
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5
CuCN (cat.)
84%
O
(racemic)
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RO
O
6c, R = H
17, R = TBS
TBSCl
99%
HO
HO
OsO4 (cat.)
NMO
1) KIO4
MeCN/THF/H2O
35 °C, 9 h
2) NaBH4
47%
MeCN/THF/H2O
(4 : 2 : 1)
O
TBSO
O
91%
18
HO
1) Bu4NF
O
HO
2) KIO4
35 °C
O
O
O
HO
O
TBSO
PCC
MeCN/THF/H2O
20
19
91% from 19
O
NaOAc
93%
O
O
O
7c
Scheme 4 Synthesis of the lignan intermediate 7c.
OMe
O
ArMgBr
5
Cu cat.
LiCl
(racemic)
HO
21
75%
OMe
O
route B
X
7d, X = O
22, X = NH
O
Scheme 5 Synthesis of the rolipram intermediate 7d.
In summary, we have established a new method for syn-
thesis of b-substituted g-butyrolactones. Although we fo-
cused mainly on lactones with an arylmethyl group at the
b-position, the present method undoubtedly will be appli-
cable to synthesis of other lactones possessing an aryl
group or an alkyl group.
Acknowledgment
This work was supported by a Grant-in-Aid for Scientific Research
from the Ministry of Education, Science, Sports, and Culture, Ja-
pan.
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M. G.; Kobayashi, Y. J. Org. Chem. 2001, 66, 5881.
Synlett 2004, No. 11, 1941–1944 © Thieme Stuttgart · New York