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

Research output: Contribution to journal › Article › peer-review

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

ASJC Scopus subject areas

Biochemistry
Organic Chemistry
Drug Discovery

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Methylation-ring opening of 3,3-disubstituted 2,3-epoxy alcohols. Synthesis of chiral quaternary fragments for assembly of briaran diterpenes. / Balasubramaniam, Rajiv P.; Moss, David K.; Wyatt, Justin K.; Spence, John D.; Gee, Arvin; Nantz, Michael H.

In: Tetrahedron, Vol. 53, No. 22, 02.06.1997, p. 7429-7444.

Research output: Contribution to journal › Article › peer-review

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

Abstract

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