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Synfacts 2009(8): 0936-0936  
DOI: 10.1055/s-0029-1217498
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Traceless Solid-Phase Synthesis of cis-Decalins

Contributor(s): Yasuhiro Uozumi, Yoichi M. A. Yamada, Chung Keun Jin
M. Yoshida, C. Hedberg, M. Kaiser, H. Waldmann*
Max-Planck-Institut für Molekulare Physiologie, Dortmund, Technische Universität Dortmund and Chemical Genomics Centre der Max-Planck-Gesellschaft, Dortmund, Germany
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Publikationsdatum:
23. Juli 2009 (online)

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Significance

A traceless solid-phase synthesis of cis-decalins was reported. Thus, the solid-supported diene 3, prepared from 1 (7 steps), underwent the Diels-Alder reaction to give the cis-decalin derivatives. The 5-thiotetrazole linker group was cleaved with metal-assisted SN2′-type allylic substitution to give a variety of functionalized cis-decalines (8-12).