1248
G. Sabitha et al.
OH
OH
O
Catalyst
10% Pd/C
O
OTMS
O
CHO
O
+
O
8
8
8
THF,-78 °C
EtOAc
r.t, 10 h
rac-Muricatacin4
rac-3d
Tridecanal
2
OH
OH
O
10% Pd/C
Catalyst
O
OTMS
O
CHO
O
+
O
3
3
3
THF,-78 °C
EtOAc
r.t, 10 h
Hexanal
2
rac-3e
-L-factor 5
rac
Scheme 2
7. Dalpiaz A, Pavan B, Scaglianti M, Vitali F, Bortolotti F, Biondi
C, Scatturin A, Manfredini S (2005) Indian J Pharmacy 291:171
8. Kobayashi S, Sugiura M, Kitagawa H, Lam WWL (2002) Chem
Rev 102:2227
concentrated under reduced pressure and purified by silica
gel column chromatography to obtain the pure product 3.
General procedure for the preparation of compounds 4
and 5
9. Kobayashi S, Hamada T, Nagayama S, Kanabe K (2001) Org Lett
3:165
10. Kobayashi S, Hachiya I, Takahori T (1993) Synthesis 371
11. Kobayashi S, Hachiya I (1992) Tetrahedron Lett 33:1625
12. Rassu G, Zanardi F, Battistini L, Casiraghi G (1999) Synlett 1333
13. Casiraghi G, Rassu G (1995) Synthesis 607
14. Jefford CW, Jaggi D, Boukouvalas J (1987) Tetrahedron Lett
28:4037
15. Acocella MR, De Rosa M, Massa A, Palombi L, Villano R,
Scettri A (2005) Tetrahedron 61:4091
16. Kong K, Romo D (2006) Org Lett 8:2909
17. Yoshii E, Koizumi T, Kitatsuji E, Kawazoe T, Kaneko T (1976)
Heterocycles 4:1663
To a stirred solution of 3e (0.2 g, 1.08 mmol) in 10 cm3
EtOAc, 10% Pd/C (50 mg) was added, and the reaction
mixture was stirred under H2 atmosphere for 10 h at room
temperature and then filtered through Celite. The filtrate
was concentrated under reduced pressure to yield com-
pound 5 (0.18 g, 89%) as a colorless liquid. A similar
procedure was used for the preparation of compound 4.
18. Boukouvalas J, Maltais F, Lachance N (1994) Tetrahedron Lett
35:7897
19. Lopez CS, Alvarez RAA, Vaz B, Faza ON, de Lera AR (2005) J
Org Chem 70:3654
Acknowledgments M.N.P. thanks CSIR, New Delhi, for the award
of a fellowship. M.R. thanks IICT, Hyderabad for providing facilities.
20. For a recent organocatalytic approach, see: De Rosa M, Citro L,
Soriente A (2006) Tetrahedron Lett 47:8507
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