A short approach to chaetomellic anhydride A from 2,2-dichloropalmitic acid: elucidation of the mechanism governing the functional rearrangement of the chlorinated pyrrolidin-2-one intermediate

F  Bellesia; C  Danieli; L  De Buyck; R  Galeazzi; F  Ghelfi; A  Mucci; M  Orena; U M  Pagnoni; A F  Parsons; F  Roncaglia

doi:10.1016/j.tet.2005.09.140

A short approach to chaetomellic anhydride A from 2,2-dichloropalmitic acid: elucidation of the mechanism governing the functional rearrangement of the chlorinated pyrrolidin-2-one intermediate

F Bellesia, C Danieli, L De Buyck, R Galeazzi, F Ghelfi, A Mucci, M Orena, U M Pagnoni, A F Parsons, F Roncaglia

Chemistry

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

Abstract

Chaetomellic anhydride A was efficiently attained in three steps, starting from 2,2-dichloropalmitic acid and 2-(3-chloro-2-propenylamino)pyridine. Atom transfer radical cyclisation selectively formed the cis-stereoisomer of the trichloropyrrolidin-2-one, which underwent a stereospecific functional rearrangement to form a substituted maleimide. The choice of 2-pyridyl, as 'cyclisation auxiliary' in the atom transfer radical cyclisation step, proved beneficial for hydrolysis of the maleimide to form the desired anhydride. (c) 2005 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	746-757
Number of pages	12
Journal	Tetrahedron
Volume	62
Issue number	4
DOIs	https://doi.org/10.1016/j.tet.2005.09.140
Publication status	Published - 23 Jan 2006

Keywords

halocompound
pyrrolidinone
radical reaction
rearrangement
FARNESYL-PROTEIN TRANSFERASE
TRANSFER RADICAL CYCLIZATION
STEREOSELECTIVE-SYNTHESIS
DIMETHYLMALEIC ANHYDRIDE
MOLECULAR MECHANICS
EFFICIENT SYNTHESIS
FACILE SYNTHESIS
GAMMA-LACTAMS
CUCL-TMEDA
ANALOGS

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10.1016/j.tet.2005.09.140

Cite this

Bellesia, F., Danieli, C., De Buyck, L., Galeazzi, R., Ghelfi, F., Mucci, A., Orena, M., Pagnoni, U. M., Parsons, A. F., & Roncaglia, F. (2006). A short approach to chaetomellic anhydride A from 2,2-dichloropalmitic acid: elucidation of the mechanism governing the functional rearrangement of the chlorinated pyrrolidin-2-one intermediate. Tetrahedron, 62(4), 746-757. https://doi.org/10.1016/j.tet.2005.09.140

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title = "A short approach to chaetomellic anhydride A from 2,2-dichloropalmitic acid: elucidation of the mechanism governing the functional rearrangement of the chlorinated pyrrolidin-2-one intermediate",

abstract = "Chaetomellic anhydride A was efficiently attained in three steps, starting from 2,2-dichloropalmitic acid and 2-(3-chloro-2-propenylamino)pyridine. Atom transfer radical cyclisation selectively formed the cis-stereoisomer of the trichloropyrrolidin-2-one, which underwent a stereospecific functional rearrangement to form a substituted maleimide. The choice of 2-pyridyl, as 'cyclisation auxiliary' in the atom transfer radical cyclisation step, proved beneficial for hydrolysis of the maleimide to form the desired anhydride. (c) 2005 Elsevier Ltd. All rights reserved.",

keywords = "halocompound, pyrrolidinone, radical reaction, rearrangement, FARNESYL-PROTEIN TRANSFERASE, TRANSFER RADICAL CYCLIZATION, STEREOSELECTIVE-SYNTHESIS, DIMETHYLMALEIC ANHYDRIDE, MOLECULAR MECHANICS, EFFICIENT SYNTHESIS, FACILE SYNTHESIS, GAMMA-LACTAMS, CUCL-TMEDA, ANALOGS",

author = "F Bellesia and C Danieli and {De Buyck}, L and R Galeazzi and F Ghelfi and A Mucci and M Orena and Pagnoni, {U M} and Parsons, {A F} and F Roncaglia",

year = "2006",

month = jan,

day = "23",

doi = "10.1016/j.tet.2005.09.140",

language = "English",

volume = "62",

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journal = "Tetrahedron",

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Bellesia, F, Danieli, C, De Buyck, L, Galeazzi, R, Ghelfi, F, Mucci, A, Orena, M, Pagnoni, UM, Parsons, AF & Roncaglia, F 2006, 'A short approach to chaetomellic anhydride A from 2,2-dichloropalmitic acid: elucidation of the mechanism governing the functional rearrangement of the chlorinated pyrrolidin-2-one intermediate', Tetrahedron, vol. 62, no. 4, pp. 746-757. https://doi.org/10.1016/j.tet.2005.09.140

TY - JOUR

T1 - A short approach to chaetomellic anhydride A from 2,2-dichloropalmitic acid: elucidation of the mechanism governing the functional rearrangement of the chlorinated pyrrolidin-2-one intermediate

AU - Bellesia, F

AU - Danieli, C

AU - De Buyck, L

AU - Galeazzi, R

AU - Ghelfi, F

AU - Mucci, A

AU - Orena, M

AU - Pagnoni, U M

AU - Parsons, A F

AU - Roncaglia, F

PY - 2006/1/23

Y1 - 2006/1/23

N2 - Chaetomellic anhydride A was efficiently attained in three steps, starting from 2,2-dichloropalmitic acid and 2-(3-chloro-2-propenylamino)pyridine. Atom transfer radical cyclisation selectively formed the cis-stereoisomer of the trichloropyrrolidin-2-one, which underwent a stereospecific functional rearrangement to form a substituted maleimide. The choice of 2-pyridyl, as 'cyclisation auxiliary' in the atom transfer radical cyclisation step, proved beneficial for hydrolysis of the maleimide to form the desired anhydride. (c) 2005 Elsevier Ltd. All rights reserved.

AB - Chaetomellic anhydride A was efficiently attained in three steps, starting from 2,2-dichloropalmitic acid and 2-(3-chloro-2-propenylamino)pyridine. Atom transfer radical cyclisation selectively formed the cis-stereoisomer of the trichloropyrrolidin-2-one, which underwent a stereospecific functional rearrangement to form a substituted maleimide. The choice of 2-pyridyl, as 'cyclisation auxiliary' in the atom transfer radical cyclisation step, proved beneficial for hydrolysis of the maleimide to form the desired anhydride. (c) 2005 Elsevier Ltd. All rights reserved.

KW - halocompound

KW - pyrrolidinone

KW - radical reaction

KW - rearrangement

KW - FARNESYL-PROTEIN TRANSFERASE

KW - TRANSFER RADICAL CYCLIZATION

KW - STEREOSELECTIVE-SYNTHESIS

KW - DIMETHYLMALEIC ANHYDRIDE

KW - MOLECULAR MECHANICS

KW - EFFICIENT SYNTHESIS

KW - FACILE SYNTHESIS

KW - GAMMA-LACTAMS

KW - CUCL-TMEDA

KW - ANALOGS

U2 - 10.1016/j.tet.2005.09.140

DO - 10.1016/j.tet.2005.09.140

M3 - Article

VL - 62

SP - 746

EP - 757

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 4

ER -