The specific epimerisation of phthalideisoquinoline alkaloids

Mehdi M Baradarani; Rolf H Prager

doi:10.1016/S0040-4039(99)01315-5

The specific epimerisation of phthalideisoquinoline alkaloids

Mehdi M Baradarani, Rolf H Prager

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

4 Citations (Scopus)

Abstract

1R,9S α-Narcotine has been converted to 1S,9S β-narcotine by reaction with thiophosgene, followed by sodium acetate in acetic acid. Conversion to 1R,9R β-narcotine was achieved by sequential reaction of α-narcotine with α-chloroethyl chlorothionoformate, followed by aqueous sodium hydroxide. Finally, 1R,9R β-narcotine was converted to 1S,9R α-narcotine by reaction with thiophosgene, followed by sodium acetate in acetic acid.

Original language	English
Pages (from-to)	7403-7406
Number of pages	4
Journal	Tetrahedron Letters
Volume	40
Issue number	41
DOIs	https://doi.org/10.1016/S0040-4039(99)01315-5
Publication status	Published - 8 Oct 1999

Keywords

Benzylic cleavage of amines
Chlorothionoformate
Phthalideisoquinolines
Thiophosgene

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title = "The specific epimerisation of phthalideisoquinoline alkaloids",

abstract = "1R,9S α-Narcotine has been converted to 1S,9S β-narcotine by reaction with thiophosgene, followed by sodium acetate in acetic acid. Conversion to 1R,9R β-narcotine was achieved by sequential reaction of α-narcotine with α-chloroethyl chlorothionoformate, followed by aqueous sodium hydroxide. Finally, 1R,9R β-narcotine was converted to 1S,9R α-narcotine by reaction with thiophosgene, followed by sodium acetate in acetic acid.",

keywords = "Benzylic cleavage of amines, Chlorothionoformate, Phthalideisoquinolines, Thiophosgene",

author = "Baradarani, {Mehdi M} and Prager, {Rolf H}",

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doi = "10.1016/S0040-4039(99)01315-5",

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T1 - The specific epimerisation of phthalideisoquinoline alkaloids

AU - Baradarani, Mehdi M

AU - Prager, Rolf H

PY - 1999/10/8

Y1 - 1999/10/8

N2 - 1R,9S α-Narcotine has been converted to 1S,9S β-narcotine by reaction with thiophosgene, followed by sodium acetate in acetic acid. Conversion to 1R,9R β-narcotine was achieved by sequential reaction of α-narcotine with α-chloroethyl chlorothionoformate, followed by aqueous sodium hydroxide. Finally, 1R,9R β-narcotine was converted to 1S,9R α-narcotine by reaction with thiophosgene, followed by sodium acetate in acetic acid.

AB - 1R,9S α-Narcotine has been converted to 1S,9S β-narcotine by reaction with thiophosgene, followed by sodium acetate in acetic acid. Conversion to 1R,9R β-narcotine was achieved by sequential reaction of α-narcotine with α-chloroethyl chlorothionoformate, followed by aqueous sodium hydroxide. Finally, 1R,9R β-narcotine was converted to 1S,9R α-narcotine by reaction with thiophosgene, followed by sodium acetate in acetic acid.

KW - Benzylic cleavage of amines

KW - Chlorothionoformate

KW - Phthalideisoquinolines

KW - Thiophosgene

UR - http://www.scopus.com/inward/record.url?scp=0033536615&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(99)01315-5

DO - 10.1016/S0040-4039(99)01315-5

M3 - Article

AN - SCOPUS:0033536615

SN - 0040-4039

VL - 40

SP - 7403

EP - 7406

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 41

ER -

The specific epimerisation of phthalideisoquinoline alkaloids

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Keywords

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