A new route to (+/-)-erythro-roccellic acid and chaetomellic anhydride C through functional rearrangement, promoted by n-propylamine or CH3ONa/CH3OH, of N-propyl-3-chloro-4-dichloromethyl-3-dodecylpyrrolidin-2-one

L  De Buyck; C  Danieli; F  Ghelfi; U M  Pagnoni; A F  Parsons; M  Pattarozzi; F  Roncaglia

doi:10.1016/j.tet.2005.01.086

A new route to (+/-)-erythro-roccellic acid and chaetomellic anhydride C through functional rearrangement, promoted by n-propylamine or CH3ONa/CH3OH, of N-propyl-3-chloro-4-dichloromethyl-3-dodecylpyrrolidin-2-one

L De Buyck, C Danieli, F Ghelfi, U M Pagnoni, A F Parsons, M Pattarozzi, F Roncaglia

Chemistry

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

Abstract

The rearrangement of a trichloro-pyrrolidin-2-one, prepared by the CuCl-TMEDA catalyzed atom transfer radical cyclization of N-alkyl-N-(3-chloro-2-propenyl)-2,2-dichloromyristamide, with n-propylamine or CH3ONa/CH3OH, is the key step of a new, short and inexpensive route to chaetomellic anhydride C and (+/-)-erythro-roccellic acid. (c) 2005 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	2871-2877
Number of pages	7
Journal	Tetrahedron
Volume	61
Issue number	11
DOIs	https://doi.org/10.1016/j.tet.2005.01.086
Publication status	Published - 14 Mar 2005

Keywords

radicals
cyclizations
pyrrolidinones
rearrangements
PROTEIN TRANSFERASE INHIBITOR
CHEMISTRY
LICHEN
PYRROLIDIN-2-ONES
ANALOGS

Access to Document

10.1016/j.tet.2005.01.086

Cite this

De Buyck, L., Danieli, C., Ghelfi, F., Pagnoni, U. M., Parsons, A. F., Pattarozzi, M., & Roncaglia, F. (2005). A new route to (+/-)-erythro-roccellic acid and chaetomellic anhydride C through functional rearrangement, promoted by n-propylamine or CH3ONa/CH3OH, of N-propyl-3-chloro-4-dichloromethyl-3-dodecylpyrrolidin-2-one. Tetrahedron, 61(11), 2871-2877. https://doi.org/10.1016/j.tet.2005.01.086

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title = "A new route to (+/-)-erythro-roccellic acid and chaetomellic anhydride C through functional rearrangement, promoted by n-propylamine or CH3ONa/CH3OH, of N-propyl-3-chloro-4-dichloromethyl-3-dodecylpyrrolidin-2-one",

abstract = "The rearrangement of a trichloro-pyrrolidin-2-one, prepared by the CuCl-TMEDA catalyzed atom transfer radical cyclization of N-alkyl-N-(3-chloro-2-propenyl)-2,2-dichloromyristamide, with n-propylamine or CH3ONa/CH3OH, is the key step of a new, short and inexpensive route to chaetomellic anhydride C and (+/-)-erythro-roccellic acid. (c) 2005 Elsevier Ltd. All rights reserved.",

keywords = "radicals, cyclizations, pyrrolidinones, rearrangements, PROTEIN TRANSFERASE INHIBITOR, CHEMISTRY, LICHEN, PYRROLIDIN-2-ONES, ANALOGS",

author = "{De Buyck}, L and C Danieli and F Ghelfi and Pagnoni, {U M} and Parsons, {A F} and M Pattarozzi and F Roncaglia",

year = "2005",

month = mar,

day = "14",

doi = "10.1016/j.tet.2005.01.086",

language = "English",

volume = "61",

pages = "2871--2877",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier",

number = "11",

}

De Buyck, L, Danieli, C, Ghelfi, F, Pagnoni, UM, Parsons, AF, Pattarozzi, M & Roncaglia, F 2005, 'A new route to (+/-)-erythro-roccellic acid and chaetomellic anhydride C through functional rearrangement, promoted by n-propylamine or CH3ONa/CH3OH, of N-propyl-3-chloro-4-dichloromethyl-3-dodecylpyrrolidin-2-one', Tetrahedron, vol. 61, no. 11, pp. 2871-2877. https://doi.org/10.1016/j.tet.2005.01.086

A new route to (+/-)-erythro-roccellic acid and chaetomellic anhydride C through functional rearrangement, promoted by n-propylamine or CH3ONa/CH3OH, of N-propyl-3-chloro-4-dichloromethyl-3-dodecylpyrrolidin-2-one. / De Buyck, L ; Danieli, C ; Ghelfi, F et al.
In: Tetrahedron, Vol. 61, No. 11, 14.03.2005, p. 2871-2877.

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

TY - JOUR

T1 - A new route to (+/-)-erythro-roccellic acid and chaetomellic anhydride C through functional rearrangement, promoted by n-propylamine or CH3ONa/CH3OH, of N-propyl-3-chloro-4-dichloromethyl-3-dodecylpyrrolidin-2-one

AU - De Buyck, L

AU - Danieli, C

AU - Ghelfi, F

AU - Pagnoni, U M

AU - Parsons, A F

AU - Pattarozzi, M

AU - Roncaglia, F

PY - 2005/3/14

Y1 - 2005/3/14

N2 - The rearrangement of a trichloro-pyrrolidin-2-one, prepared by the CuCl-TMEDA catalyzed atom transfer radical cyclization of N-alkyl-N-(3-chloro-2-propenyl)-2,2-dichloromyristamide, with n-propylamine or CH3ONa/CH3OH, is the key step of a new, short and inexpensive route to chaetomellic anhydride C and (+/-)-erythro-roccellic acid. (c) 2005 Elsevier Ltd. All rights reserved.

AB - The rearrangement of a trichloro-pyrrolidin-2-one, prepared by the CuCl-TMEDA catalyzed atom transfer radical cyclization of N-alkyl-N-(3-chloro-2-propenyl)-2,2-dichloromyristamide, with n-propylamine or CH3ONa/CH3OH, is the key step of a new, short and inexpensive route to chaetomellic anhydride C and (+/-)-erythro-roccellic acid. (c) 2005 Elsevier Ltd. All rights reserved.

KW - radicals

KW - cyclizations

KW - pyrrolidinones

KW - rearrangements

KW - PROTEIN TRANSFERASE INHIBITOR

KW - CHEMISTRY

KW - LICHEN

KW - PYRROLIDIN-2-ONES

KW - ANALOGS

U2 - 10.1016/j.tet.2005.01.086

DO - 10.1016/j.tet.2005.01.086

M3 - Article

SN - 0040-4020

VL - 61

SP - 2871

EP - 2877

JO - Tetrahedron

JF - Tetrahedron

IS - 11

ER -