α-Acylamino radical cyclizations: Application to the synthesis of a tetracyclic substructure of gelsemine

Joong Kwon Choi, Deok-Chan Ha, David J. Hart, Chih Shone Lee, Subban Ramesh, Shung Wu

Research output: Contribution to journalArticle

46 Citations (Scopus)

Abstract

Syntheses of gelsemine substructures 2 and 3 are described. Free-radical precursors 14, 18, 35, and 38 were prepared, and their behavior upon treatment with tri-n-butyltin hydride and AIBN was examined. The radical derived from 14 afforded reduction product 15, whereas the radicals derived from 18, 35, and 38 gave cyclization products 23, 37, and 39, respectively. Aspects of these free-radical cyclizations as well as the conversion of 23 and 37 to 2 and 3, respectively, are presented.

Original languageEnglish
Pages (from-to)279-290
Number of pages12
JournalJournal of Organic Chemistry
Volume54
Issue number2
Publication statusPublished - 1989 Dec 1
Externally publishedYes

Fingerprint

Cyclization
Free Radicals
gelsemine
tributyltin
azobis(isobutyronitrile)

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

α-Acylamino radical cyclizations : Application to the synthesis of a tetracyclic substructure of gelsemine. / Choi, Joong Kwon; Ha, Deok-Chan; Hart, David J.; Lee, Chih Shone; Ramesh, Subban; Wu, Shung.

In: Journal of Organic Chemistry, Vol. 54, No. 2, 01.12.1989, p. 279-290.

Research output: Contribution to journalArticle

Choi, Joong Kwon ; Ha, Deok-Chan ; Hart, David J. ; Lee, Chih Shone ; Ramesh, Subban ; Wu, Shung. / α-Acylamino radical cyclizations : Application to the synthesis of a tetracyclic substructure of gelsemine. In: Journal of Organic Chemistry. 1989 ; Vol. 54, No. 2. pp. 279-290.
@article{ec8c87da16e54e989c52655e6de01959,
title = "α-Acylamino radical cyclizations: Application to the synthesis of a tetracyclic substructure of gelsemine",
abstract = "Syntheses of gelsemine substructures 2 and 3 are described. Free-radical precursors 14, 18, 35, and 38 were prepared, and their behavior upon treatment with tri-n-butyltin hydride and AIBN was examined. The radical derived from 14 afforded reduction product 15, whereas the radicals derived from 18, 35, and 38 gave cyclization products 23, 37, and 39, respectively. Aspects of these free-radical cyclizations as well as the conversion of 23 and 37 to 2 and 3, respectively, are presented.",
author = "Choi, {Joong Kwon} and Deok-Chan Ha and Hart, {David J.} and Lee, {Chih Shone} and Subban Ramesh and Shung Wu",
year = "1989",
month = "12",
day = "1",
language = "English",
volume = "54",
pages = "279--290",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "2",

}

TY - JOUR

T1 - α-Acylamino radical cyclizations

T2 - Application to the synthesis of a tetracyclic substructure of gelsemine

AU - Choi, Joong Kwon

AU - Ha, Deok-Chan

AU - Hart, David J.

AU - Lee, Chih Shone

AU - Ramesh, Subban

AU - Wu, Shung

PY - 1989/12/1

Y1 - 1989/12/1

N2 - Syntheses of gelsemine substructures 2 and 3 are described. Free-radical precursors 14, 18, 35, and 38 were prepared, and their behavior upon treatment with tri-n-butyltin hydride and AIBN was examined. The radical derived from 14 afforded reduction product 15, whereas the radicals derived from 18, 35, and 38 gave cyclization products 23, 37, and 39, respectively. Aspects of these free-radical cyclizations as well as the conversion of 23 and 37 to 2 and 3, respectively, are presented.

AB - Syntheses of gelsemine substructures 2 and 3 are described. Free-radical precursors 14, 18, 35, and 38 were prepared, and their behavior upon treatment with tri-n-butyltin hydride and AIBN was examined. The radical derived from 14 afforded reduction product 15, whereas the radicals derived from 18, 35, and 38 gave cyclization products 23, 37, and 39, respectively. Aspects of these free-radical cyclizations as well as the conversion of 23 and 37 to 2 and 3, respectively, are presented.

UR - http://www.scopus.com/inward/record.url?scp=0024502584&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0024502584&partnerID=8YFLogxK

M3 - Article

AN - SCOPUS:0024502584

VL - 54

SP - 279

EP - 290

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 2

ER -