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

Research output: Contribution to journalArticle

23 Citations (Scopus)

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 languageEnglish (US)
Pages (from-to)7429-7444
Number of pages16
JournalTetrahedron
Volume53
Issue number22
DOIs
StatePublished - Jun 2 1997

Fingerprint

Methylation
Diterpenes
Alcohols
Carbon

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

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 journalArticle

Balasubramaniam, Rajiv P. ; Moss, David K. ; Wyatt, Justin K. ; Spence, John D. ; Gee, Arvin ; Nantz, Michael H. / Methylation-ring opening of 3,3-disubstituted 2,3-epoxy alcohols. Synthesis of chiral quaternary fragments for assembly of briaran diterpenes. In: Tetrahedron. 1997 ; Vol. 53, No. 22. pp. 7429-7444.
@article{63180d0761e842089b2a0b3df444cc4d,
title = "Methylation-ring opening of 3,3-disubstituted 2,3-epoxy alcohols. Synthesis of chiral quaternary fragments for assembly of briaran diterpenes",
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.",
author = "Balasubramaniam, {Rajiv P.} and Moss, {David K.} and Wyatt, {Justin K.} and Spence, {John D.} and Arvin Gee and Nantz, {Michael H.}",
year = "1997",
month = "6",
day = "2",
doi = "10.1016/S0040-4020(97)00453-5",
language = "English (US)",
volume = "53",
pages = "7429--7444",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Limited",
number = "22",

}

TY - JOUR

T1 - Methylation-ring opening of 3,3-disubstituted 2,3-epoxy alcohols. Synthesis of chiral quaternary fragments for assembly of briaran diterpenes

AU - Balasubramaniam, Rajiv P.

AU - Moss, David K.

AU - Wyatt, Justin K.

AU - Spence, John D.

AU - Gee, Arvin

AU - Nantz, Michael H.

PY - 1997/6/2

Y1 - 1997/6/2

N2 - 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.

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.

UR - http://www.scopus.com/inward/record.url?scp=0030981561&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0030981561&partnerID=8YFLogxK

U2 - 10.1016/S0040-4020(97)00453-5

DO - 10.1016/S0040-4020(97)00453-5

M3 - Article

AN - SCOPUS:0030981561

VL - 53

SP - 7429

EP - 7444

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 22

ER -