An intramolecular Diels-Alder route to novel tetracyclic benzo[b]thiophene derivatives

Pilho Kim, Jennifer M. Tsuruda, Marilyn M. Olmstead, Shawn Eisenberg, Mark J. Kurth

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

A one-pot route to 3-benzo[b]thiophen-2-yl-acrylates (2) from the corresponding thiophenols (1) is reported. Ester reduction and subsequent hydroxyl esterification deliver psuedo trienoates (II) which undergo an intramolecular Diels-Alder (IMDA) reaction to give two 2-oxa-9-thiacyclopenta[b]fluoren-3-one products (I) - the major Diels-Alder product rearomatizes to 7.

Original languageEnglish (US)
Pages (from-to)3963-3966
Number of pages4
JournalTetrahedron Letters
Volume43
Issue number21
DOIs
StatePublished - May 20 2002

Fingerprint

Acrylates
Esterification
Cycloaddition Reaction
Hydroxyl Radical
Esters
Derivatives
benzothiophene
thiophenol

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Kim, P., Tsuruda, J. M., Olmstead, M. M., Eisenberg, S., & Kurth, M. J. (2002). An intramolecular Diels-Alder route to novel tetracyclic benzo[b]thiophene derivatives. Tetrahedron Letters, 43(21), 3963-3966. https://doi.org/10.1016/S0040-4039(02)00565-8

An intramolecular Diels-Alder route to novel tetracyclic benzo[b]thiophene derivatives. / Kim, Pilho; Tsuruda, Jennifer M.; Olmstead, Marilyn M.; Eisenberg, Shawn; Kurth, Mark J.

In: Tetrahedron Letters, Vol. 43, No. 21, 20.05.2002, p. 3963-3966.

Research output: Contribution to journalArticle

Kim, P, Tsuruda, JM, Olmstead, MM, Eisenberg, S & Kurth, MJ 2002, 'An intramolecular Diels-Alder route to novel tetracyclic benzo[b]thiophene derivatives', Tetrahedron Letters, vol. 43, no. 21, pp. 3963-3966. https://doi.org/10.1016/S0040-4039(02)00565-8
Kim, Pilho ; Tsuruda, Jennifer M. ; Olmstead, Marilyn M. ; Eisenberg, Shawn ; Kurth, Mark J. / An intramolecular Diels-Alder route to novel tetracyclic benzo[b]thiophene derivatives. In: Tetrahedron Letters. 2002 ; Vol. 43, No. 21. pp. 3963-3966.
@article{99e68600b2344a8c99cc854ed9f8f3e4,
title = "An intramolecular Diels-Alder route to novel tetracyclic benzo[b]thiophene derivatives",
abstract = "A one-pot route to 3-benzo[b]thiophen-2-yl-acrylates (2) from the corresponding thiophenols (1) is reported. Ester reduction and subsequent hydroxyl esterification deliver psuedo trienoates (II) which undergo an intramolecular Diels-Alder (IMDA) reaction to give two 2-oxa-9-thiacyclopenta[b]fluoren-3-one products (I) - the major Diels-Alder product rearomatizes to 7.",
author = "Pilho Kim and Tsuruda, {Jennifer M.} and Olmstead, {Marilyn M.} and Shawn Eisenberg and Kurth, {Mark J.}",
year = "2002",
month = "5",
day = "20",
doi = "10.1016/S0040-4039(02)00565-8",
language = "English (US)",
volume = "43",
pages = "3963--3966",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Limited",
number = "21",

}

TY - JOUR

T1 - An intramolecular Diels-Alder route to novel tetracyclic benzo[b]thiophene derivatives

AU - Kim, Pilho

AU - Tsuruda, Jennifer M.

AU - Olmstead, Marilyn M.

AU - Eisenberg, Shawn

AU - Kurth, Mark J.

PY - 2002/5/20

Y1 - 2002/5/20

N2 - A one-pot route to 3-benzo[b]thiophen-2-yl-acrylates (2) from the corresponding thiophenols (1) is reported. Ester reduction and subsequent hydroxyl esterification deliver psuedo trienoates (II) which undergo an intramolecular Diels-Alder (IMDA) reaction to give two 2-oxa-9-thiacyclopenta[b]fluoren-3-one products (I) - the major Diels-Alder product rearomatizes to 7.

AB - A one-pot route to 3-benzo[b]thiophen-2-yl-acrylates (2) from the corresponding thiophenols (1) is reported. Ester reduction and subsequent hydroxyl esterification deliver psuedo trienoates (II) which undergo an intramolecular Diels-Alder (IMDA) reaction to give two 2-oxa-9-thiacyclopenta[b]fluoren-3-one products (I) - the major Diels-Alder product rearomatizes to 7.

UR - http://www.scopus.com/inward/record.url?scp=0037140869&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0037140869&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(02)00565-8

DO - 10.1016/S0040-4039(02)00565-8

M3 - Article

AN - SCOPUS:0037140869

VL - 43

SP - 3963

EP - 3966

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 21

ER -