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Synthesis 2002(13): 1819-1822
DOI: 10.1055/s-2002-33911
DOI: 10.1055/s-2002-33911
PAPER
© Georg Thieme Verlag Stuttgart · New York
A New Chiral Route to Optically Pure (+)- and (-)-cis-endo-4-Oxatricyclo[5.2.1.02,6]dec-8-en-3-one
Further Information
Received
13 May 2002
Publication Date:
09 September 2002 (online)
Publication History
Publication Date:
09 September 2002 (online)
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Abstracts
cis-endo-4-Oxatricyclo[5.2.1.02,6]dec-8-en-3-one has been prepared from known chiral hydroxydicyclopentadiene by sequential oxidative cleavage of cis-oriented glycols as the key steps.
Key words
polycycles - chirality - oxidations - triols - lactones
- 1
Takano S.Inomata K.Kurotaki A.Ohkawa T.Ogasawara K. J. Chem. Soc., Chem. Commun. 1987, 1720 - 2
Suzuki K.Shoji M.Kobayashi E.Inomata K. Tetrahedron: Asymmetry 2001, 12: 2789 -
3a
Rao YS. Chem. Rev. 1964, 64: 353 -
3b
Rao YS. Chem. Rev. 1976, 76: 625 - 4
Takano S.Kurotaki A.Ogasawara K. Synthesis 1987, 1075 -
5a
Metz P. Tetrahedron 1989, 45: 7311 -
5b
Janssen AJM.Klunder AJH.Zwanenburg B. Tetrahedron Lett. 1990, 31: 7219 -
5c
Janssen AJM.Klunder AJH.Zwanenburg B. Tetrahedron 1991, 47: 5513 -
5d
Taniguchi T.Goto Y.Ogasawara K. Synlett 1997, 707 -
6a
Lok KP.Jakovac IJ.Jones JB. J. Am. Chem. Soc. 1985, 107: 2521 -
6b
Harada T.Wada I.Oku A. J. Org. Chem. 1989, 54: 2599 -
6c
Aitken RA.Gopal J. Tetrahedron: Asymmetry 1990, 1: 517 -
6d
Asensio G.Andreu C.Marco JA. Chem. Ber. 1992, 125: 2233 -
6e
Luna H.Prasad K.Repic O. Tetrahedron: Asymmetry 1994, 5: 303 -
6f
North M.Zagotto G. Synlett 1995, 639 -
6g
Seebach D.Jaeschke G.Wang YM. Angew. Chem., Int. Ed. Engl. 1995, 34: 2395 -
6h
Albers T.Biagini SCG.Hibbs DE.Hursthouse MB.Malik KMA.North M.Uriarte E.Zagotto G. Synthesis 1996, 393 -
6i
Taniguchi T.Ogasawara K. Tetrahedron Lett. 1997, 38: 433 -
6j
Jaeschke G.Seebach D. J. Org. Chem. 1998, 63: 1190 -
7a
Arai Y.Matsui M.Koizumi T. J. Chem. Soc., Perkin Trans. 1 1990, 1233 -
7b
Maruoka K.Akakura M.Saito S.Ooi T.Yamamoto H. J. Am. Chem. Soc. 1994, 116: 6153 -
9a
Tanaka K.Ogasawara K. Synthesis 1995, 1237 -
9b
Ogasawara K. J. Synth. Org. Chem. Jpn. 1996, 54: 29 -
10a
Takano S.Inomata K.Ogasawara K. Chem. Lett. 1989, 359 -
10b
Tanaka K.Ogasawara K. Synthesis 1996, 219 -
11a
Fetizon M.Golfier M.Louis J.-M. Tetrahedron 1975, 31: 171 -
11b For the preparation of
Ag2CO3 on Celite, see:
Balogh V.Fetizon M.Golfier M. J. Org. Chem. 1971, 36: 1339 - 12
Levin JI.Turos E.Weinreb SM. Synth. Commun. 1982, 12: 989
References
Preliminary results of this work were presented at The 121 st Annual Meeting of the Pharmaceutical Society of Japan Sapporo, Japan, March 28-30, 2001. See abstracts Vol. 2, 22.