Theoretical investigation of the rubicordifolin cascade

Jean Philip Lumb, Jamin L. Krinsky, Dirk Trauner

Research output: Contribution to journalArticle

Abstract

The results of a theoretical investigation on the complex cascade reaction leading to the natural product rubicordifolin are reported. These computations analyze the discrete transformations that are required during the conversion of the vinyl naphthoquinone starting material into the natural product, including two pseudopericyclic cyclizations as well as a diastereoselective, hetero-Diels-Alder reaction.

Original languageEnglish (US)
Pages (from-to)5162-5165
Number of pages4
JournalOrganic Letters
Volume12
Issue number22
DOIs
StatePublished - Nov 19 2010

Fingerprint

Biological Products
cascades
Naphthoquinones
Diels-Alder reactions
Cyclization
Cycloaddition Reaction
products
rubicordifolin

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Lumb, J. P., Krinsky, J. L., & Trauner, D. (2010). Theoretical investigation of the rubicordifolin cascade. Organic Letters, 12(22), 5162-5165. https://doi.org/10.1021/ol102157d

Theoretical investigation of the rubicordifolin cascade. / Lumb, Jean Philip; Krinsky, Jamin L.; Trauner, Dirk.

In: Organic Letters, Vol. 12, No. 22, 19.11.2010, p. 5162-5165.

Research output: Contribution to journalArticle

Lumb, JP, Krinsky, JL & Trauner, D 2010, 'Theoretical investigation of the rubicordifolin cascade', Organic Letters, vol. 12, no. 22, pp. 5162-5165. https://doi.org/10.1021/ol102157d
Lumb, Jean Philip ; Krinsky, Jamin L. ; Trauner, Dirk. / Theoretical investigation of the rubicordifolin cascade. In: Organic Letters. 2010 ; Vol. 12, No. 22. pp. 5162-5165.
@article{a7431befb66b48bbb0117dd8ad4ac9df,
title = "Theoretical investigation of the rubicordifolin cascade",
abstract = "The results of a theoretical investigation on the complex cascade reaction leading to the natural product rubicordifolin are reported. These computations analyze the discrete transformations that are required during the conversion of the vinyl naphthoquinone starting material into the natural product, including two pseudopericyclic cyclizations as well as a diastereoselective, hetero-Diels-Alder reaction.",
author = "Lumb, {Jean Philip} and Krinsky, {Jamin L.} and Dirk Trauner",
year = "2010",
month = "11",
day = "19",
doi = "10.1021/ol102157d",
language = "English (US)",
volume = "12",
pages = "5162--5165",
journal = "Organic Letters",
issn = "1523-7060",
publisher = "American Chemical Society",
number = "22",

}

TY - JOUR

T1 - Theoretical investigation of the rubicordifolin cascade

AU - Lumb, Jean Philip

AU - Krinsky, Jamin L.

AU - Trauner, Dirk

PY - 2010/11/19

Y1 - 2010/11/19

N2 - The results of a theoretical investigation on the complex cascade reaction leading to the natural product rubicordifolin are reported. These computations analyze the discrete transformations that are required during the conversion of the vinyl naphthoquinone starting material into the natural product, including two pseudopericyclic cyclizations as well as a diastereoselective, hetero-Diels-Alder reaction.

AB - The results of a theoretical investigation on the complex cascade reaction leading to the natural product rubicordifolin are reported. These computations analyze the discrete transformations that are required during the conversion of the vinyl naphthoquinone starting material into the natural product, including two pseudopericyclic cyclizations as well as a diastereoselective, hetero-Diels-Alder reaction.

UR - http://www.scopus.com/inward/record.url?scp=78449286725&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=78449286725&partnerID=8YFLogxK

U2 - 10.1021/ol102157d

DO - 10.1021/ol102157d

M3 - Article

C2 - 20973524

AN - SCOPUS:78449286725

VL - 12

SP - 5162

EP - 5165

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 22

ER -