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

Rajiv P. Balasubramaniam; David K. Moss; Justin K. Wyatt; John D. Spence; Arvin Gee; Michael H. Nantz

doi:10.1016/S0040-4020(97)00453-5

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

Rajiv P. Balasubramaniam, David K. Moss, Justin K. Wyatt, John D. Spence, Arvin Gee, Michael H. Nantz

Chemistry

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23 Scopus citations

Abstract

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.

Original language	English (US)
Pages (from-to)	7429-7444
Number of pages	16
Journal	Tetrahedron
Volume	53
Issue number	22
DOIs	https://doi.org/10.1016/S0040-4020(97)00453-5
State	Published - Jun 2 1997

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ASJC Scopus subject areas

Biochemistry
Organic Chemistry
Drug Discovery

Cite this

Balasubramaniam, R. P., Moss, D. K., Wyatt, J. K., Spence, J. D., Gee, A., & Nantz, M. H. (1997). Methylation-ring opening of 3,3-disubstituted 2,3-epoxy alcohols. Synthesis of chiral quaternary fragments for assembly of briaran diterpenes. Tetrahedron, 53(22), 7429-7444. https://doi.org/10.1016/S0040-4020(97)00453-5

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abstract = "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.",

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AU - Moss, David K.

AU - Wyatt, Justin K.

AU - Spence, John D.

AU - Gee, Arvin

AU - Nantz, Michael H.

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AB - 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.

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10.1016/S0040-4020(97)00453-5