A synthesis of (-)-tashiromine and formal synthesis of (+)-tashiromine utilizing a highly enantioselective pyrrole/cobaloxime π-cation cyclization

Jennifer L. Gage, Bruce Branchaud

Research output: Contribution to journalArticle

52 Citations (Scopus)

Abstract

Cyclization of (5-N-pyrrolyl-2-hydroxypentyl)cobaloxime (13) proceeds by intramolecular electrophilic aromatic substitution of a cobaloxime π-cation onto the pyrrole ring to provide 6-exo cyclization product (14) in 95% yield. This cyclization is highly enantioselective. It is applied to a synthesis of highly enantioenriched (-)-tashiromine, (-)-21, and a formal synthesis of (+)-tashiromine.

Original languageEnglish (US)
Pages (from-to)7007-7010
Number of pages4
JournalTetrahedron Letters
Volume38
Issue number40
DOIs
StatePublished - Oct 6 1997
Externally publishedYes

Fingerprint

Pyrroles
Cyclization
Cations
Substitution reactions
cobaloxime
tashiromine

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

@article{78313542919342179a882c9420ec30c9,
title = "A synthesis of (-)-tashiromine and formal synthesis of (+)-tashiromine utilizing a highly enantioselective pyrrole/cobaloxime π-cation cyclization",
abstract = "Cyclization of (5-N-pyrrolyl-2-hydroxypentyl)cobaloxime (13) proceeds by intramolecular electrophilic aromatic substitution of a cobaloxime π-cation onto the pyrrole ring to provide 6-exo cyclization product (14) in 95{\%} yield. This cyclization is highly enantioselective. It is applied to a synthesis of highly enantioenriched (-)-tashiromine, (-)-21, and a formal synthesis of (+)-tashiromine.",
author = "Gage, {Jennifer L.} and Bruce Branchaud",
year = "1997",
month = "10",
day = "6",
doi = "10.1016/S0040-4039(97)01638-9",
language = "English (US)",
volume = "38",
pages = "7007--7010",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Limited",
number = "40",

}

TY - JOUR

T1 - A synthesis of (-)-tashiromine and formal synthesis of (+)-tashiromine utilizing a highly enantioselective pyrrole/cobaloxime π-cation cyclization

AU - Gage, Jennifer L.

AU - Branchaud, Bruce

PY - 1997/10/6

Y1 - 1997/10/6

N2 - Cyclization of (5-N-pyrrolyl-2-hydroxypentyl)cobaloxime (13) proceeds by intramolecular electrophilic aromatic substitution of a cobaloxime π-cation onto the pyrrole ring to provide 6-exo cyclization product (14) in 95% yield. This cyclization is highly enantioselective. It is applied to a synthesis of highly enantioenriched (-)-tashiromine, (-)-21, and a formal synthesis of (+)-tashiromine.

AB - Cyclization of (5-N-pyrrolyl-2-hydroxypentyl)cobaloxime (13) proceeds by intramolecular electrophilic aromatic substitution of a cobaloxime π-cation onto the pyrrole ring to provide 6-exo cyclization product (14) in 95% yield. This cyclization is highly enantioselective. It is applied to a synthesis of highly enantioenriched (-)-tashiromine, (-)-21, and a formal synthesis of (+)-tashiromine.

UR - http://www.scopus.com/inward/record.url?scp=0030875301&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0030875301&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(97)01638-9

DO - 10.1016/S0040-4039(97)01638-9

M3 - Article

VL - 38

SP - 7007

EP - 7010

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 40

ER -