A New Chiral Route to Optically Pure (+)- and (-)-cis-endo-4-Oxatricyclo[5.2.1.02,6]dec-8-en-3-one

Katsufumi  Suzuki; Kohei  Inomata

doi:10.1055/s-2002-33911

PAPER

A New Chiral Route to Optically Pure (+)- and (-)-cis-endo-4-Oxatricyclo[5.2.1.0^2,6]dec-8-en-3-one

Katsufumi Suzuki, Kohei Inomata*
Tohoku Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai 981-8558, Japan
Fax: +81(22)2752013; e-Mail: inomata@tohoku-pharm.ac.jp;

Abstract

All articles of this category

Abstracts

cis-endo-4-Oxatricyclo[5.2.1.0^2,6]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

Full Text

References

<A NAME="RF04002SS-1">1</A> Takano S. Inomata K. Kurotaki A. Ohkawa T. Ogasawara K. J. Chem. Soc., Chem. Commun. 1987, 1720

<A NAME="RF04002SS-2">2</A> Suzuki K. Shoji M. Kobayashi E. Inomata K. Tetrahedron: Asymmetry 2001, 12: 2789

<A NAME="RF04002SS-3A">3a</A> Rao YS. Chem. Rev. 1964, 64: 353

<A NAME="RF04002SS-3B">3b</A> Rao YS. Chem. Rev. 1976, 76: 625

<A NAME="RF04002SS-4">4</A> Takano S. Kurotaki A. Ogasawara K. Synthesis 1987, 1075

<A NAME="RF04002SS-5A">5a</A> Metz P. Tetrahedron 1989, 45: 7311

<A NAME="RF04002SS-5B">5b</A> Janssen AJM. Klunder AJH. Zwanenburg B. Tetrahedron Lett. 1990, 31: 7219

<A NAME="RF04002SS-5C">5c</A> Janssen AJM. Klunder AJH. Zwanenburg B. Tetrahedron 1991, 47: 5513

<A NAME="RF04002SS-5D">5d</A> Taniguchi T. Goto Y. Ogasawara K. Synlett 1997, 707

<A NAME="RF04002SS-6A">6a</A> Lok KP. Jakovac IJ. Jones JB. J. Am. Chem. Soc. 1985, 107: 2521

<A NAME="RF04002SS-6B">6b</A> Harada T. Wada I. Oku A. J. Org. Chem. 1989, 54: 2599

<A NAME="RF04002SS-6C">6c</A> Aitken RA. Gopal J. Tetrahedron: Asymmetry 1990, 1: 517

<A NAME="RF04002SS-6D">6d</A> Asensio G. Andreu C. Marco JA. Chem. Ber. 1992, 125: 2233

<A NAME="RF04002SS-6E">6e</A> Luna H. Prasad K. Repic O. Tetrahedron: Asymmetry 1994, 5: 303

<A NAME="RF04002SS-6F">6f</A> North M. Zagotto G. Synlett 1995, 639

<A NAME="RF04002SS-6G">6g</A> Seebach D. Jaeschke G. Wang YM. Angew. Chem., Int. Ed. Engl. 1995, 34: 2395

<A NAME="RF04002SS-6H">6h</A> Albers T. Biagini SCG. Hibbs DE. Hursthouse MB. Malik KMA. North M. Uriarte E. Zagotto G. Synthesis 1996, 393

<A NAME="RF04002SS-6I">6i</A> Taniguchi T. Ogasawara K. Tetrahedron Lett. 1997, 38: 433

<A NAME="RF04002SS-6J">6j</A> Jaeschke G. Seebach D. J. Org. Chem. 1998, 63: 1190

<A NAME="RF04002SS-7A">7a</A> Arai Y. Matsui M. Koizumi T. J. Chem. Soc., Perkin Trans. 1 1990, 1233

<A NAME="RF04002SS-7B">7b</A> Maruoka K. Akakura M. Saito S. Ooi T. Yamamoto H. J. Am. Chem. Soc. 1994, 116: 6153

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.

<A NAME="RF04002SS-9A">9a</A> Tanaka K. Ogasawara K. Synthesis 1995, 1237

<A NAME="RF04002SS-9B">9b</A> Ogasawara K. J. Synth. Org. Chem. Jpn. 1996, 54: 29

<A NAME="RF04002SS-10A">10a</A> Takano S. Inomata K. Ogasawara K. Chem. Lett. 1989, 359

<A NAME="RF04002SS-10B">10b</A> Tanaka K. Ogasawara K. Synthesis 1996, 219

<A NAME="RF04002SS-11A">11a</A> Fetizon M. Golfier M. Louis J.-M. Tetrahedron 1975, 31: 171

<A NAME="RF04002SS-11B">11b</A> For the preparation of Ag₂CO₃ on Celite, see: Balogh V. Fetizon M. Golfier M. J. Org. Chem. 1971, 36: 1339

<A NAME="RF04002SS-12">12</A> Levin JI. Turos E. Weinreb SM. Synth. Commun. 1982, 12: 989