Catalytic iron-mediated ene carbocyclizations of trienes: enantioselective syntheses of the iridoid monoterpenes (-)-mitsugashiwalactone and (+)-isoiridomyrmecin

James M. Takacs, Young Chan Myoung

Research output: Contribution to journalArticle

51 Citations (Scopus)

Abstract

The iron-catalyzed cycloisomerization of a chiral (2E,7E) 2,7,9-decatriene derivative bearing a methyl substituent adjacent to the 1,3-diene subunit proceeds with high levels of 1,2-stereoinduction relative to the resident methyl-bearing stereocenter. The stereochemistry of the chiral cyclopentane product is proven by conversion to (-)-Mitsugashiwalactone (1) and to (+)-Isoiridomyrmecin (2).

Original languageEnglish (US)
Pages (from-to)317-320
Number of pages4
JournalTetrahedron Letters
Volume33
Issue number3
DOIs
StatePublished - Jan 14 1992

Fingerprint

Bearings (structural)
Cyclopentanes
Monoterpenes
Iron
Stereochemistry
Derivatives
isoiridomyrmecin

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

@article{395d3948d4a349929e9b789fd66896cd,
title = "Catalytic iron-mediated ene carbocyclizations of trienes: enantioselective syntheses of the iridoid monoterpenes (-)-mitsugashiwalactone and (+)-isoiridomyrmecin",
abstract = "The iron-catalyzed cycloisomerization of a chiral (2E,7E) 2,7,9-decatriene derivative bearing a methyl substituent adjacent to the 1,3-diene subunit proceeds with high levels of 1,2-stereoinduction relative to the resident methyl-bearing stereocenter. The stereochemistry of the chiral cyclopentane product is proven by conversion to (-)-Mitsugashiwalactone (1) and to (+)-Isoiridomyrmecin (2).",
author = "Takacs, {James M.} and Myoung, {Young Chan}",
year = "1992",
month = "1",
day = "14",
doi = "10.1016/S0040-4039(00)74120-7",
language = "English (US)",
volume = "33",
pages = "317--320",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Limited",
number = "3",

}

TY - JOUR

T1 - Catalytic iron-mediated ene carbocyclizations of trienes

T2 - enantioselective syntheses of the iridoid monoterpenes (-)-mitsugashiwalactone and (+)-isoiridomyrmecin

AU - Takacs, James M.

AU - Myoung, Young Chan

PY - 1992/1/14

Y1 - 1992/1/14

N2 - The iron-catalyzed cycloisomerization of a chiral (2E,7E) 2,7,9-decatriene derivative bearing a methyl substituent adjacent to the 1,3-diene subunit proceeds with high levels of 1,2-stereoinduction relative to the resident methyl-bearing stereocenter. The stereochemistry of the chiral cyclopentane product is proven by conversion to (-)-Mitsugashiwalactone (1) and to (+)-Isoiridomyrmecin (2).

AB - The iron-catalyzed cycloisomerization of a chiral (2E,7E) 2,7,9-decatriene derivative bearing a methyl substituent adjacent to the 1,3-diene subunit proceeds with high levels of 1,2-stereoinduction relative to the resident methyl-bearing stereocenter. The stereochemistry of the chiral cyclopentane product is proven by conversion to (-)-Mitsugashiwalactone (1) and to (+)-Isoiridomyrmecin (2).

UR - http://www.scopus.com/inward/record.url?scp=0026586323&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0026586323&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(00)74120-7

DO - 10.1016/S0040-4039(00)74120-7

M3 - Article

AN - SCOPUS:0026586323

VL - 33

SP - 317

EP - 320

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 3

ER -