Y. Matsumura et al. / Tetrahedron Letters 45 (2004) 9131–9134
9133
O
O
OBz
OBn
O
OBz
OBn
O
i
ii
iii
D-1e
95%
97%
93%
BnO
BnO
OH
O
THP
4
5
OH
O
O
O
O
OPO3H2
OH
HO
HO
OBn
ð3Þ
OH
O
P
O
O
v
iv
OBn
100%
97%
BnO
OBn
OBn
THP
BnO
OH
O
THP
3
6
7
(i) 2,2-Dimethoxypropane (6.4 equiv), p-TsOH (2 mol%), acetone, rt. (ii) 3,4-Didehydro-2H-pyran (2.4
equiv), p-TsOH (1.4 mol%), CH2Cl2, rt. (iii) KOH (3 equiv), HOCH2CH2OH, rt. (iv) (a) 1H-Tetrazole (2
equiv), dibenzyl diisopropylphosphoramidite (1.5 equiv), CH Cl , rt; (b) m-CPBA (3 equiv), CH Cl , 0 C.
˚
2
2
2
2
(v) 10% Pd/C, MeOH/H2O (80/20), H2, rt.
Maeda, N.;Mikoshiba, K. Nature 1989, 342, 32–38;(d)
Berridge, M. J.;Irvine, R. F. Nature 1989, 341, 197–205;
(e) Mignery, G. A.;Newton, C. L.;Archer, B. T., III;
Sudhof, T. C. J. Biol. Chem. 1990, 265, 12679–12685;(f)
¨
Berridge, M. J. Nature 1993, 361, 315–325.
Acknowledgements
Y.M. and T.M. thank the Ministry of Education,
Science, and Culture, Japan, respectively, for financial
support (Scientific Research in Priority Areas 420 and
No. 14771245).
5. (a) Ferrier, R. J.;Middleton, S. Chem. Rev. 1993, 93,
2779–2831;(b) Falck, J. R.;Abdali, A. Biomed. Chem.
Lett. 1993, 3, 717–720;(c) Reddy, K. K.;Saady, M.;
Falck, J. R.;Whited, G. J. Org. Chem. 1995, 60, 3385–
References and notes
´
3390;(d) Dorma n, J. C. G.;Prestwich, G. D. J. Org.
Chem. 1996, 61, 393–397;(e) Profit, J. C. A. A.;Prestwich,
G. D. J. Org. Chem. 1996, 61, 6305–6312;(f) Colobert, F.;
Tito, A.;Khiar, N.;Denni, D.;Medina, M. A.;Martin-
1. For examples of review: (a) Kagan, H. B.;Fiaud, J. C.
Top. Stereochem. 1988, 18, 249–330;(b) Yamaguchi, M.;
Hirama, M. Chemtracts: Org. Chem. 1994, 7, 401–405;(c)
´
Lomas, M.;Ruana, J.-L. G.;Solladie , G. J. Org. Chem.
Noyori, R.;Tokunaga, M.;Kitamura, M.
Bull. Chem.
1998, 63, 8918–8921;(g) Conrad, R. M.;Grogan, M. J.;
Bertozzi, C. R. Org. Lett. 2002, 4, 1359–1361.
Soc. Jpn. 1995, 68, 36–56;(d) Cook, G. R. Curr. Org.
Chem. 2000, 4, 869–885;(e) Nicholas, K. M.;Ferreira, E.
M.;Stoltz, B. M.;Jensen, D. R.;Pugsley, J. S.;Sigman,
M. S. Chemtracts 2001, 14, 654–658.
6. (a) Chida, N.;Yamada, E.;Ogawa, S.
J. Carbohydr.
´
Chem. 1988, 7, 555–570;(b) Brusik, K. S.;Salamon czyk,
G. M. Carbohydr. Res. 1989, 195, 67–73;(c) Pietrusiewicz,
K. M.;Salamonczyk, G. M.;Bruzik, K. S.;Wieczorek, W.
Tetrahedron 1992, 26, 5523–5542;(d) Brusik, K. S.;Tsai,
M. D. J. Am. Chem. Soc. 1992, 114, 6361–6374;(e) Bruzik,
K. S.;Myers, J.;Tsai, M.-D. Tetrahedron Lett. 1992, 33,
1009–1012;(f) Chida, N.;Koizumi, K.;Kitada, Y.;
Yokoyama, C.;Ogawa, S. J. Chem. Soc., Chem. Commun.
1994, 111–113;(g) Brusik, K. S.;Kubiak, R. J. Tetrahe-
dron Lett. 1995, 36, 2415–2418;(h) Mills, S. J.;Potter, B.
V. L. J. Org. Chem. 1996, 61, 8980–8987.
2. Recent examples of kinetic resolution of alcohols: (a)
Vedejs, E.;Daugulis, O.;Diver, S. T. J. Org. Chem. 1996,
61, 430–431;(b) Ruble, J. C.;Fu, G. C. J. Org. Chem.
1996, 61, 7230–7231;(c) Oriyama, T.;Hori, Y.;Imai, K.;
Sasaki, R. Tetrahedron Lett. 1996, 37, 8543–8546;(d)
Ruble, J. C.;Latham, H. A.;Fu, G. C. J. Am. Chem. Soc.
1997, 119, 1492–1493;(e) Kawabata, T.;Nagato, M.;
Takasu, K.;Fuji, K. J. Am. Chem. Soc. 1997, 119, 3169–
3170;(f) Copeland, G. T.;Jarvo, E. R.;Miller, S. J. J. Org.
Chem. 1998, 63, 6784–6785;(g) Vedejs, E.;Mackay, J. A.
Org. Lett. 2001, 3, 535–536;(h) Sekar, G.;Nishiyama, H.
J. Am. Chem. Soc. 2001, 123, 3603–3604;(i) Copeland, G.
T.;Miller, S. J. J. Am. Chem. Soc. 2001, 123, 6496–6502;
(j) Vedejs, E.;MacKay, J. A. Org. Lett. 2001, 3, 535–536;
(k) Lin, M.-H.;RajanBabu, T. V. Org. Lett. 2002, 4, 1607–
1610;(l) Vedejs, E.;Daugulis, O. J. Am. Chem. Soc. 2003,
125, 4166–4173;(m) Priem, G.;Pelotier, B.;Macdonald, S.
J. F.;Anson, M. S.;Campbell, I. B. J. Org. Chem. 2003,
68, 3844–3848;(n) Pelotier, B.;Priem, G.;Campbell, I. B.;
Macdonald, S. J. F.;Anson, M. S. Synlett 2003, 679–683;
(o) Spivey, A. C.;Leese, D. P.;Zhu, F.;Davey, S. G.;
Jarvest, R. L. Tetrahedron 2004, 60, 4513–4525.
7. (a) Gou, D.-M.;Liu, Y.-C.;Chen, C.-S. Carbohydr. Res.
1992, 234, 51–64;(b) Gou, D.-M.;Chen, C.-S. Tetrahe-
dron Lett. 1992, 33, 721–724;(c) Laumen, K.;Ghisalba, O.
Biosci. Biotech. Biochem. 1994, 58, 2046–2049;(d) Watan-
abe, Y.;Tomioka, M.;Ozaki, S. Tetrahedron 1995, 51,
8969–8976.
8. (a) Trost, B. M.;Patterson, D. E.;Hembre, E. J. J. Am.
Chem. Soc. 1999, 121, 10834–10835;(b) Sculimbrene, B.
R.;Miller, S. J. J. Am. Chem. Soc. 2001, 123, 10125–
10126;(c) Sculimbrene, B. R.;Morgan, A. J.;Miller, S. J.
J. Am. Chem. Soc. 2002, 124, 11653–11656.
9. (a) Lee, H. W.;Kishi, Y. J. Org. Chem. 1985, 50, 4402–
4404;(b) Baudin, G.;Gla nzer, B. I.;Swaminathan, S.;
¨
3. Matsumura, Y.;Maki, T.;Murakami, S.;Onomura, O.
J. Am. Chem. Soc. 2003, 125, 2052–2053.
4. (a) Berridge, M. J. Ann. Rev. Biochem. 1987, 56, 159–193;
(b) Supattapone, S.;Worley, P. F.;Baraban, J. M.;
Synder, S. H. J. Biol. Chem. 1988, 263, 1530–1534;(c)
Furuichi, T.;Yoshikawa, S.;Miyawaki, A.;Wada, K.;
Vasella, A. Helv. Chim. Acta 1988, 71, 1367–1378.
10. (a) Evans, D. A.;Rovis, T.;Johnson, J. S. Pure Appl.
Chem. 1999, 71, 1407–1415;Johnson, J. S.;Evans, D. A.
Acc. Chem. Res. 2000, 33, 325–335.
11. A typical experimental procedure for benzoylation of
D,L-1a–d: Benzoyl chloride (0.5equiv) was added into a