Methylation-ring opening of 3,3-disubstituted 2,3-epoxy alcohols. Synthesis of chiral quaternary fragments for assembly of briaran diterpenes

Two chiral quaternary carbon-containing fragments suitable for elaboration to the briaran diterpenes were obtained by regioselective methylation of functionalized 3,3-disubstituted 2,3-epoxy-1-ols. The factors which favor methylation at the more hindered position of a trisubstituted 2,3-epoxy alcoho...

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Bibliographic Details
Published in:Tetrahedron 1997-06, Vol.53 (22), p.7429-7444
Main Authors: Balasubramaniam, Rajiv P., Moss, David K., Wyatt, Justin K., Spence, John D., Gee, Arvin, Nantz, Michael H.
Format: Article
Language:English
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Summary:Two chiral quaternary carbon-containing fragments suitable for elaboration to the briaran diterpenes were obtained by regioselective methylation of functionalized 3,3-disubstituted 2,3-epoxy-1-ols. The factors which favor methylation at the more hindered position of a trisubstituted 2,3-epoxy alcohol were determined. Regioselective methylation of 3,3-disubstituted 2,3-epoxy-1-ols established the C(1) and C(8) quaternary centers of the briaran ten-membered ring.
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(97)00453-5