Cyclization of α,δ-Dihydroxyepoxide Derivatives. Stereochemical Studies

D. Díez; R. F. Moro; W. Lumeras; L. Rodríguez; I. S. Marcos; P. Basabe; R. Escarcena; J. G. Urones

doi:10.1055/s-2002-19792

PAPER

Cyclization of α,δ-Dihydroxyepoxide Derivatives. Stereochemical Studies

D. Díez*, R. F. Moro, W. Lumeras, L. Rodríguez, I. S. Marcos, P. Basabe, R. Escarcena, J. G. Urones
Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad de Salamanca, Plaza de los Caídos 1-5, 37008, Salamanca, Spain
Fax: +34(923)294574; e-Mail: ddm@usal.es;

Abstract

All articles of this category

Abstract

The influence of different protecting groups in the cyclization of highly substituted α,δ-dihydroxyepoxides has been studied. It is possible to control the opening or the cyclization of the epoxide depending on the protecting group used.

Key words

tetrahydropyrans - epoxides - cyclization - stereochemistry

Full Text

References

For reviews see:

<A NAME="RE06101SS-1A">1a</A> Yasumoto T. Musata M. Chem. Rev. 1993, 93: 1897

<A NAME="RE06101SS-1B">1b</A> Shimizu Y. Chem. Rev. 1993, 93: 1685

<A NAME="RE06101SS-1C">1c</A> Scheuer PJ. Tetrahedron 1994, 50: 3

<A NAME="RE06101SS-2A">2a</A> Gruttadauria M. Aprile C. Serena Riela S. Noto R. Tetrahedron Lett. 2001, 42: 2213

<A NAME="RE06101SS-2D">2d</A> Vidari G. Di Rosa A. Zanoni G. Bicchi C. Tetrahedron Asymmetry 1999, 10: 3547

For leading references see:

<A NAME="RE06101SS-3A">3a</A> Gillaume P. Baylon C. Heck MP. Mioskowski C. Tetrahedron Lett. 2000, 41: 3829

<A NAME="RE06101SS-3B">3b</A> Vidari G. Di Rosa A. Castronovo F. Zanoni G. Tetrahedron Asymmetry 2000, 11: 981

<A NAME="RE06101SS-3C">3c</A> Crotti P. Di Bussolo V. Favero L. Pineschi M. Marianucci F. Renzi G. Amici G. Roselli G. Tetrahedron 2000, 56: 7513

<A NAME="RE06101SS-3D">3d</A> Benedetti F. Berti F. Norberdo S. Tetrahedron Lett. 1998, 39: 7971

<A NAME="RE06101SS-3E">3e</A> Nicolaou KC. Prasad CVC. Somers PK. Hwang CK. J. Am. Chem. Soc. 1989, 111: 5335

<A NAME="RE06101SS-4A">4a</A> Mukai C. Ikeda Y. Hanaoku M. Tetrahedron Lett. 1994, 35: 2179

<A NAME="RE06101SS-4B">4b</A> Suzuki T. Sato O. Hirama M. Tetrahedron Lett. 1990, 31: 4747

<A NAME="RE06101SS-5">5</A> Garcia C. Soler MA. Martin VS. Tetrahedron Lett. 2000, 41: 4127

For leading references see:

<A NAME="RE06101SS-6A">6a</A> Chautemps P. Pierre JL. Tetrahedron 1976, 32: 549

<A NAME="RE06101SS-6B">6b</A> Rossiter BE. Verhoeven TR. Sharpless KB. Tetrahedron Lett. 1979, 4733

<A NAME="RE06101SS-7">7</A> Díez Martin D. Marcos IS. Basabe P. Romero RE. Moro R. Lumeras W. Rodríguez L. Urones JG. Synthesis 2001, 1013

<A NAME="RE06101SS-8">8</A> Díez Martin D. Moro RF. Lumeras W. Rodríguez L. Marcos I. Basabe P. Romero RE. Urones JG. Synlett 2001, 1332