Application of the TMSOTf-AgClO4 activator system to the synthesis of novel, potent, C-10 phenoxy derivatives of dihydroartemisinin

Paul M. O' Neill; Alison Miller; Steve Ward; B. Kevin Park; Feodor Scheinmann; Andrew V. Stachulski

doi:10.1016/s0040-4039(99)01891-2

Application of the TMSOTf-AgClO4 activator system to the synthesis of novel, potent, C-10 phenoxy derivatives of dihydroartemisinin

Paul M. O' Neill
, Alison Miller
, Steve Ward
, B. Kevin Park
, Feodor Scheinmann
, Andrew V. Stachulski

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

28 Citations (Scopus)

Abstract

The combination of TMSOTf and AgClO4 promotes the efficient C-10 phenoxylation of dihydroartemisinin (3) in good chemical yield and excellent stereoselectivity. In contrast to previous reports on other phenoxyglycoside derivatives, the phenoxy derivatives (5a-11b) of dihydroartemisinin do not undergo O to C rearrangement to the corresponding C-10-aryl derivatives. All of the new derivatives had potent in vitro antimalarial activity.

Original language	English
Pages (from-to)	9129-9132
Number of pages	4
Journal	Tetrahedron Letters
Volume	40
Issue number	51
DOIs	https://doi.org/10.1016/s0040-4039(99)01891-2
Publication status	Published - 17 Dec 1999
Externally published	Yes

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title = "Application of the TMSOTf-AgClO4 activator system to the synthesis of novel, potent, C-10 phenoxy derivatives of dihydroartemisinin",

abstract = "The combination of TMSOTf and AgClO4 promotes the efficient C-10 phenoxylation of dihydroartemisinin (3) in good chemical yield and excellent stereoselectivity. In contrast to previous reports on other phenoxyglycoside derivatives, the phenoxy derivatives (5a-11b) of dihydroartemisinin do not undergo O to C rearrangement to the corresponding C-10-aryl derivatives. All of the new derivatives had potent in vitro antimalarial activity.",

author = "\{O' Neill\}, \{Paul M.\} and Alison Miller and Steve Ward and \{Kevin Park\}, B. and Feodor Scheinmann and Stachulski, \{Andrew V.\}",

year = "1999",

month = dec,

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doi = "10.1016/s0040-4039(99)01891-2",

language = "English",

volume = "40",

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journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd",

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TY - JOUR

T1 - Application of the TMSOTf-AgClO4 activator system to the synthesis of novel, potent, C-10 phenoxy derivatives of dihydroartemisinin

AU - O' Neill, Paul M.

AU - Miller, Alison

AU - Ward, Steve

AU - Kevin Park, B.

AU - Scheinmann, Feodor

AU - Stachulski, Andrew V.

PY - 1999/12/17

Y1 - 1999/12/17

N2 - The combination of TMSOTf and AgClO4 promotes the efficient C-10 phenoxylation of dihydroartemisinin (3) in good chemical yield and excellent stereoselectivity. In contrast to previous reports on other phenoxyglycoside derivatives, the phenoxy derivatives (5a-11b) of dihydroartemisinin do not undergo O to C rearrangement to the corresponding C-10-aryl derivatives. All of the new derivatives had potent in vitro antimalarial activity.

AB - The combination of TMSOTf and AgClO4 promotes the efficient C-10 phenoxylation of dihydroartemisinin (3) in good chemical yield and excellent stereoselectivity. In contrast to previous reports on other phenoxyglycoside derivatives, the phenoxy derivatives (5a-11b) of dihydroartemisinin do not undergo O to C rearrangement to the corresponding C-10-aryl derivatives. All of the new derivatives had potent in vitro antimalarial activity.

U2 - 10.1016/s0040-4039(99)01891-2

DO - 10.1016/s0040-4039(99)01891-2

M3 - Article

SN - 0040-4039

VL - 40

SP - 9129

EP - 9132

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 51

ER -

Application of the TMSOTf-AgClO4 activator system to the synthesis of novel, potent, C-10 phenoxy derivatives of dihydroartemisinin

Abstract

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