A simple and efficient route to chaetomellic anhydride A: A potent natural Ras farnesyl-protein transferase inhibitor

L  De Buyck; R  Cagnoli; F  Ghelfi; G  Merighi; A  Mucci; U M  Pagnoni; A F  Parsons

doi:10.1055/s-2004-829116

A simple and efficient route to chaetomellic anhydride A: A potent natural Ras farnesyl-protein transferase inhibitor

L De Buyck, R Cagnoli, F Ghelfi, G Merighi, A Mucci, U M Pagnoni, A F Parsons

Chemistry

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

Abstract

A new and efficient approach to chaetomellic anhydride A has been devised starting from 2,2-dichloropalmitic acid. This involves the atom transfer radical cyclization of an N-alkyl-N-(3-chloro-2-propenyl)amide followed by rearrangement of the resulting trichloro-pyrrolidin-2-one.

Original language	English
Pages (from-to)	1680-1686
Number of pages	7
Journal	SYNTHESIS-STUTTGART
Issue number	10
DOIs	https://doi.org/10.1055/s-2004-829116
Publication status	Published - 5 Jul 2004

Keywords

amides
cyclisations
halogenation
pyrrolidinones
radical reactions
TRANSFER RADICAL CYCLIZATION
FACILE SYNTHESIS
ACID-A
FARNESYLTRANSFERASE INHIBITORS
CUCL-TMEDA
ANALOGS
REARRANGEMENT
N-ALLYL-N-BENZYL-2,2-DIHALOAMIDES
CHLORINATION

Access to Document

10.1055/s-2004-829116

Cite this

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title = "A simple and efficient route to chaetomellic anhydride A: A potent natural Ras farnesyl-protein transferase inhibitor",

abstract = "A new and efficient approach to chaetomellic anhydride A has been devised starting from 2,2-dichloropalmitic acid. This involves the atom transfer radical cyclization of an N-alkyl-N-(3-chloro-2-propenyl)amide followed by rearrangement of the resulting trichloro-pyrrolidin-2-one.",

keywords = "amides, cyclisations, halogenation, pyrrolidinones, radical reactions, TRANSFER RADICAL CYCLIZATION, FACILE SYNTHESIS, ACID-A, FARNESYLTRANSFERASE INHIBITORS, CUCL-TMEDA, ANALOGS, REARRANGEMENT, N-ALLYL-N-BENZYL-2,2-DIHALOAMIDES, CHLORINATION",

author = "{De Buyck}, L and R Cagnoli and F Ghelfi and G Merighi and A Mucci and Pagnoni, {U M} and Parsons, {A F}",

year = "2004",

month = jul,

day = "5",

doi = "10.1055/s-2004-829116",

language = "English",

pages = "1680--1686",

journal = "SYNTHESIS-STUTTGART",

issn = "0039-7881",

publisher = "Georg Thieme Verlag",

number = "10",

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TY - JOUR

T1 - A simple and efficient route to chaetomellic anhydride A: A potent natural Ras farnesyl-protein transferase inhibitor

AU - De Buyck, L

AU - Cagnoli, R

AU - Ghelfi, F

AU - Merighi, G

AU - Mucci, A

AU - Pagnoni, U M

AU - Parsons, A F

PY - 2004/7/5

Y1 - 2004/7/5

N2 - A new and efficient approach to chaetomellic anhydride A has been devised starting from 2,2-dichloropalmitic acid. This involves the atom transfer radical cyclization of an N-alkyl-N-(3-chloro-2-propenyl)amide followed by rearrangement of the resulting trichloro-pyrrolidin-2-one.

AB - A new and efficient approach to chaetomellic anhydride A has been devised starting from 2,2-dichloropalmitic acid. This involves the atom transfer radical cyclization of an N-alkyl-N-(3-chloro-2-propenyl)amide followed by rearrangement of the resulting trichloro-pyrrolidin-2-one.

KW - amides

KW - cyclisations

KW - halogenation

KW - pyrrolidinones

KW - radical reactions

KW - TRANSFER RADICAL CYCLIZATION

KW - FACILE SYNTHESIS

KW - ACID-A

KW - FARNESYLTRANSFERASE INHIBITORS

KW - CUCL-TMEDA

KW - ANALOGS

KW - REARRANGEMENT

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

KW - CHLORINATION

U2 - 10.1055/s-2004-829116

DO - 10.1055/s-2004-829116

M3 - Article

SN - 0039-7881

SP - 1680

EP - 1686

JO - SYNTHESIS-STUTTGART

JF - SYNTHESIS-STUTTGART

IS - 10

ER -