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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 34, 2004 - Issue 21
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Original Articles

Synthesis of the First α‐Fluoro‐Phosphotyrosyl Mimetic

Zhen‐Dan Shi Laboratory of Medicinal Chemistry, Center for Cancer Research, National Cancer Institute, National Institutes of Health, NCI‐Frederick, P.O. Box B, Bldg. 376 Boyles St., Frederick, Maryland, 20702‐1201, USA
,
Hongpeng Liu Department of Hematology/Oncology, University of Michigan Medical School, Ann Arbor, Michigan, USA
,
Manchao Zhang Department of Hematology/Oncology, University of Michigan Medical School, Ann Arbor, Michigan, USA
,
Dajun Yang Department of Hematology/Oncology, University of Michigan Medical School, Ann Arbor, Michigan, USA
&
Terrence R. Burke Jr. Laboratory of Medicinal Chemistry, Center for Cancer Research, National Cancer Institute, National Institutes of Health, NCI‐Frederick, P.O. Box B, Bldg. 376 Boyles St., Frederick, Maryland, 20702‐1201, USACorrespondence[email protected]
Pages 3883-3889 | Received 25 Jun 2004, Published online: 10 Jan 2011
 
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Abstract

The diastereoselective preparation of (2S)‐2‐fluoro‐4‐[[bis(1,1‐dimethylethoxy)phosphinyl]methyl] benzenepropanoic acid (5) is presented as new phosphotyrosyl (pTyr) mimetic suitably protected for incorporation into peptides. Synthesis of 5 utilized electrophilic fluorination under chiral induction provided by the commercially available Evans auxiliary, (S)‐(+)‐4‐phenyl‐2‐oxazolidinone. In order to demonstrate its synthetic utility, analogue 5 was employed to prepare a signal transduction‐directed tripeptide. The design considerations for this peptide and its preliminary biological evaluation are included.

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