Synthesis of phosphinate analogues of the phospholipid anti-tumour agent hexadecylphosphocholine (miltefosine)

Marios S. Markoulides; Andrew C. Regan

doi:10.1016/j.tetlet.2011.03.107

Synthesis of phosphinate analogues of the phospholipid anti-tumour agent hexadecylphosphocholine (miltefosine)

Marios S. Markoulides, Andrew C. Regan

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Abstract

Efficient synthesis of phosphinate analogues (in six steps and 68-69% overall yields) of the anti-tumour agent miltefosine are reported, which involve a radical hydrophosphinylation addition reaction followed by conversion to the P(III) silyloxy intermediate and Michael-type addition as the key steps. © 2011 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	2954-2956
Number of pages	2
Journal	Tetrahedron Letters
Volume	52
Issue number	23
DOIs	https://doi.org/10.1016/j.tetlet.2011.03.107
Publication status	Published - 8 Jun 2011

Keywords

Anti-tumour agents
Carbon-phosphorus bonds
Miltefosine
Phosphinic acids
Phospholipid analogues
Radical hydrophosphinylation reaction
Silyl phosphonites

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abstract = "Efficient synthesis of phosphinate analogues (in six steps and 68-69% overall yields) of the anti-tumour agent miltefosine are reported, which involve a radical hydrophosphinylation addition reaction followed by conversion to the P(III) silyloxy intermediate and Michael-type addition as the key steps. {\textcopyright} 2011 Elsevier Ltd. All rights reserved.",

keywords = "Anti-tumour agents, Carbon-phosphorus bonds, Miltefosine, Phosphinic acids, Phospholipid analogues, Radical hydrophosphinylation reaction, Silyl phosphonites",

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AU - Markoulides, Marios S.

AU - Regan, Andrew C.

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Y1 - 2011/6/8

N2 - Efficient synthesis of phosphinate analogues (in six steps and 68-69% overall yields) of the anti-tumour agent miltefosine are reported, which involve a radical hydrophosphinylation addition reaction followed by conversion to the P(III) silyloxy intermediate and Michael-type addition as the key steps. © 2011 Elsevier Ltd. All rights reserved.

AB - Efficient synthesis of phosphinate analogues (in six steps and 68-69% overall yields) of the anti-tumour agent miltefosine are reported, which involve a radical hydrophosphinylation addition reaction followed by conversion to the P(III) silyloxy intermediate and Michael-type addition as the key steps. © 2011 Elsevier Ltd. All rights reserved.

KW - Anti-tumour agents

KW - Carbon-phosphorus bonds

KW - Miltefosine

KW - Phosphinic acids

KW - Phospholipid analogues

KW - Radical hydrophosphinylation reaction

KW - Silyl phosphonites

U2 - 10.1016/j.tetlet.2011.03.107

DO - 10.1016/j.tetlet.2011.03.107

M3 - Article

SN - 1873-3581

VL - 52

SP - 2954

EP - 2956

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 23

ER -

Synthesis of phosphinate analogues of the phospholipid anti-tumour agent hexadecylphosphocholine (miltefosine)

Abstract

Keywords

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