A novel short approach to (Z)-Pulchellalactam through transition-metal-catalyzed atom-transfer radical cyclization of 1-isopropylprop-2-enyl dichloroacetate

Fulvia Felluga; Franco Ghelfi; Ugo M. Pagnoni; Andrew F. Parsons; Mariella Pattarozzi; Fabrizio Roncaglia; Ennio Valentin

doi:10.1055/s-2007-983709

A novel short approach to (Z)-Pulchellalactam through transition-metal-catalyzed atom-transfer radical cyclization of 1-isopropylprop-2-enyl dichloroacetate

Fulvia Felluga, Franco Ghelfi, Ugo M. Pagnoni, Andrew F. Parsons, Mariella Pattarozzi, Fabrizio Roncaglia, Ennio Valentin

Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

A new, five-step route to (Z)-pulchelialactam, a CD45 protein tyrosine phosphatase inhibitor, is presented. Key steps are the copper(I) chloride bipyridyl catalyzed atom-transfer radical cyclization of an appropriate allyl alpha,alpha-dichloroacetate and the subsequent dehydrochlorination/prototropic rearrangement of the resulting dichlorolactone.

Original language	English
Pages (from-to)	1882-1886
Number of pages	5
Journal	SYNTHESIS-STUTTGART
Issue number	12
DOIs	https://doi.org/10.1055/s-2007-983709
Publication status	Published - 18 Jun 2007

Keywords

cyclizations
eliminations
lactams
lactones
radical reactions
TYROSINE-PHOSPHATASE INHIBITOR
FUNGUS COROLLOSPORA-PULCHELLA
LYMPHOCYTE-ACTIVATION
FACILE SYNTHESIS
GAMMA-LACTONES
CUCL-TMEDA
CD45
N-ALLYL-N-BENZYL-2,2-DIHALOAMIDES
REARRANGEMENT
HETEROCYCLES

Access to Document

10.1055/s-2007-983709

Cite this

@article{066f88ae2b4b43d894956cb70845bb2d,

title = "A novel short approach to (Z)-Pulchellalactam through transition-metal-catalyzed atom-transfer radical cyclization of 1-isopropylprop-2-enyl dichloroacetate",

abstract = "A new, five-step route to (Z)-pulchelialactam, a CD45 protein tyrosine phosphatase inhibitor, is presented. Key steps are the copper(I) chloride bipyridyl catalyzed atom-transfer radical cyclization of an appropriate allyl alpha,alpha-dichloroacetate and the subsequent dehydrochlorination/prototropic rearrangement of the resulting dichlorolactone.",

keywords = "cyclizations, eliminations, lactams, lactones, radical reactions, TYROSINE-PHOSPHATASE INHIBITOR, FUNGUS COROLLOSPORA-PULCHELLA, LYMPHOCYTE-ACTIVATION, FACILE SYNTHESIS, GAMMA-LACTONES, CUCL-TMEDA, CD45, N-ALLYL-N-BENZYL-2,2-DIHALOAMIDES, REARRANGEMENT, HETEROCYCLES",

author = "Fulvia Felluga and Franco Ghelfi and Pagnoni, {Ugo M.} and Parsons, {Andrew F.} and Mariella Pattarozzi and Fabrizio Roncaglia and Ennio Valentin",

year = "2007",

month = jun,

day = "18",

doi = "10.1055/s-2007-983709",

language = "English",

pages = "1882--1886",

journal = "SYNTHESIS-STUTTGART",

issn = "0039-7881",

publisher = "Georg Thieme Verlag",

number = "12",

}

TY - JOUR

T1 - A novel short approach to (Z)-Pulchellalactam through transition-metal-catalyzed atom-transfer radical cyclization of 1-isopropylprop-2-enyl dichloroacetate

AU - Felluga, Fulvia

AU - Ghelfi, Franco

AU - Pagnoni, Ugo M.

AU - Parsons, Andrew F.

AU - Pattarozzi, Mariella

AU - Roncaglia, Fabrizio

AU - Valentin, Ennio

PY - 2007/6/18

Y1 - 2007/6/18

N2 - A new, five-step route to (Z)-pulchelialactam, a CD45 protein tyrosine phosphatase inhibitor, is presented. Key steps are the copper(I) chloride bipyridyl catalyzed atom-transfer radical cyclization of an appropriate allyl alpha,alpha-dichloroacetate and the subsequent dehydrochlorination/prototropic rearrangement of the resulting dichlorolactone.

AB - A new, five-step route to (Z)-pulchelialactam, a CD45 protein tyrosine phosphatase inhibitor, is presented. Key steps are the copper(I) chloride bipyridyl catalyzed atom-transfer radical cyclization of an appropriate allyl alpha,alpha-dichloroacetate and the subsequent dehydrochlorination/prototropic rearrangement of the resulting dichlorolactone.

KW - cyclizations

KW - eliminations

KW - lactams

KW - lactones

KW - radical reactions

KW - TYROSINE-PHOSPHATASE INHIBITOR

KW - FUNGUS COROLLOSPORA-PULCHELLA

KW - LYMPHOCYTE-ACTIVATION

KW - FACILE SYNTHESIS

KW - GAMMA-LACTONES

KW - CUCL-TMEDA

KW - CD45

KW - N-ALLYL-N-BENZYL-2,2-DIHALOAMIDES

KW - REARRANGEMENT

KW - HETEROCYCLES

U2 - 10.1055/s-2007-983709

DO - 10.1055/s-2007-983709

M3 - Article

SN - 0039-7881

SP - 1882

EP - 1886

JO - SYNTHESIS-STUTTGART

JF - SYNTHESIS-STUTTGART

IS - 12

ER -