Abstract
2,3,4a,6,8a-Penta-acetoxy decahydronaphthalene has been synthesised starting from 1,2,3,4-tetrahydronaphthalen-2-ol. The Birch reduction of 1,2,3,4-tetrahydronaphthalen-2-ol gave a high yield of 1,2,3,4,5,8-hexahydronaphthalen-2-ol which was acetylated. The OsO4 oxidation of the 1,2,3,4,5,8-hexahydronaphthalen-2-yl acetate followed by further acetylation gave the pentaacetates.
References
1.
Heightman T.D.
, and
Vasella A. T.
, Angew. Chem., Int. Ed. Engl. , 1999 , 38 , 750 .
2.
Jacob G.S.
, Curr. Opin. Struct. Biol. , 1995 , 5 , 605 .
3.
Suami T.
, and
Ogawa S.
, Adv. Carbohydr. Chem. Biochem. , 1990 , 48 , 21 .
4.
Suami T.
, Top. Curr. Chem. , 1990 , 154 , 257 .
5.
Hudlicky T.
,
Entwisetly D. A.
,
Pitzer K. K.
, and
Thorpe A. J.
, Chem. Rev. , 1996 , 96 , 1195 .
6.
Kiddle J.J.
, Chem. Rev. , 1995 , 95 , 2189 .
7.
Mehta G.
, and
Ramesh S. S.
, Chem. Commun. , 2000 , 2429 .
8.
Mehta G.
, and
Ramesh S. S.
, Tetrahedron Lett. , 2001 , 42 , 1987 .
9.
Zeying Z.
, and
Mingzhe Z.
, Jiegou Huaxue , 1987 , 6 , 128 .
10.
Kelebekli L.
,
Kara Y.
, and
Balci M.
, Carbohydr. Res. , 2005 , 340 , 1940 .
11.
Billington D.C.
,
Perron-Sierra F.
,
Picard I.
,
Beaubras S.
,
Duhault J.
,
Espinal J.
, and
Challal S.
, Bioorg. Med. Chem. Lett. , 1994 , 4 , 2307 .
12.
Desjardins M.
,
Lallemand M. C.
,
Hudlicky T.
, and
Abboud K. A.
, Synlett , 1997 , 728 .
13.
Mehta G.
, and
Reddy D. S.
, Tetrahedron Lett. , 1999 , 40 , 9137 .
14.
Mehta G.
,
Reddy D. S.
,
Ramesh S. S.
, and
Tatu U.
, Tetrahedron Lett. , 1999 , 40 , 9141 .
15.
Kelebekli L.
, J. Chem. Res. , 2008 , 2 , 104 .
16.
Kelebekli L.
, J. Chem. Res. , 2007 , 11 , 626 .
17.
Desjardins M.
,
Lallemand M. C.
,
Freeman S.
,
Hudlicky T.
, and
Abboud K. A.
, J. Chem. Soc. Perkin Trans 1 , 1999 , 621 .
18.
Lallemand M.C.
,
Desjardins M.
,
Freeman S.
, and
Hudlicky T.
, Tetrahedron Lett. , 1997 , 38 , 7693 .
19.
Goksu S.
,
Secen H.
, and
Sutbeyaz Y.
, Helv. Chim. Acta , 2006 , 89 , 270 .
20.
Goksu S.
,
Kazaz C.
,
Sutbeyaz Y.
, and
Secen H.
, Helv. Chim. Acta , 2003 , 86 , 3310 .
21.
Sims J.J.
, J. Org. Chem. , 1967 , 32 , 1751 .
22.Rigaku/MSC, Inc. , 9009 New Trails Drive , The Woodlands, TX 77381 USA.
23.
Sheldrick G.M.
, SHELXS97 and SHELXL97 , University of Göttingen , Germany , 1997 .