Feryan Ahmed
University of Minnesota
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Featured researches published by Feryan Ahmed.
Tetrahedron Letters | 1998
Feryan Ahmed; Craig J. Forsyth
Abstract A convergent synthesis of the C31C46 domain of the phorboxazole natural products has been developed. This involved the preparation of a C39C46 dienyl iodide and a C31C37 aldehyde, followed by their CrCl 2 -mediated coupling and final installation of the C46 ( E )-vinyl bromide via an alkyne hydrostannation-bromination sequence.
Journal of the American Chemical Society | 2011
Bo Wang; T. Matthew Hansen; Ting Wang; Dimao Wu; Lynn Weyer; Lu Ying; Mary M. Engler; Melissa Sanville; Christopher J. Leitheiser; Mathias Christmann; Yingtao Lu; Jiehao Chen; Nicholas Zunker; Russell D. Cink; Feryan Ahmed; Chi-Sing Lee; Craig J. Forsyth
The phorboxazole natural products are among the most potent inhibitors of cancer cell division, but they are essentially unavailable from natural sources at present. Laboratory syntheses based upon tri-component fragment coupling strategies have been developed that provide phorboxazole A and analogues in a reliable manner and with unprecedented efficiency. This has been orchestrated to occur via the sequential or simultaneous formation of both of the natural products oxazole moieties from two serine-derived amides, involving oxidation-cyclodehydrations. The optimized preparation of three pre-assembled components, representing carbons 3-17, 18-30, and 31-46, has been developed. This article details the design and syntheses of these three essential building blocks. The convergent coupling approach is designed to facilitate the incorporation of structural changes within each component to generate unnatural analogues, targeting those with enhanced therapeutic potential and efficacy.
Journal of the American Chemical Society | 2011
Bo Wang; T. Matthew Hansen; Lynn Weyer; Dimao Wu; Ting Wang; Mathias Christmann; Yingtao Lu; Lu Ying; Mary M. Engler; Russell D. Cink; Chi-Sing Lee; Feryan Ahmed; Craig J. Forsyth
The phorboxazoles are mixed non-ribosomal peptide synthase/polyketide synthase biosynthetic products that embody polyketide domains joined via two serine-derived oxazole moieties. Total syntheses of phorboxazole A and analogues have been developed that rely upon the convergent coupling of three fragments via biomimetically inspired de novo oxazole formation. First, the macrolide-containing domain of phorboxazole A was assembled from C3-C17 and C18-C30 building blocks via formation of the C16-C18 oxazole, followed by macrolide ring closure involving an intramolecular Still-Genarri olefination at C2-C3. Alternatively, a ring-closing metathesis process was optimized to deliver the natural products (2Z)-acrylate with remarkable geometrical selectivity. The C31-C46 side-chain domain was then appended to the macrolide by a second serine amide-derived oxazole assembly. Minimal deprotection then afforded phorboxazole A. This generally effective strategy was then dramatically abbreviated by employing a total synthesis approach wherein both of the natural products oxazole moieties were installed simultaneously. A key bis-amide precursor to the bis-oxazole was formed in a chemoselective one-pot, bis-amidation sequence without the use of amino or carboxyl protecting groups. Thereafter, both oxazoles were formed from the key C18 and C31 bis-N-(1-hydroxyalkan-2-yl)amide in a simultaneous fashion, involving oxidation-cyclodehydrations. This synthetic strategy provides a total synthesis of phorboxazole A in 18% yield over nine steps from C3-C17 and C18-C30 synthetic fragments. It illustrates the utility of a synthetic design to form a mixed non-ribosomal peptide synthase/polyketide synthase biosynthetic product based upon biomimetic oxazole formation initiated by amide bond formation to join synthetic building blocks.
Journal of the American Chemical Society | 1998
Craig J. Forsyth; Feryan Ahmed; Russell D. Cink; Chi-Sing Lee
Archive | 2011
Yo Matsuo; Shoji Hisada; Yusuke Nakamura; Feryan Ahmed; Raymond Huntley; Joel R. Walker; Helene Decornez
Archive | 2009
Mitsuaki Ohtani; Yo Matsuo; Yingfu Li; Joel R. Walker; David Jenkins; Feryan Ahmed; Ryuji Ohsawa; Shoji Hisada
Archive | 2002
Fatih M. Uckun; Rama Krishna Narla; Craig J. Forsyth; Chi-Sing Lee; Feryan Ahmed; Russell D. Cink
Tetrahedron Letters | 2014
Raymond Huntley; Mahender Gurram; Joel R. Walker; David Jenkins; Emmanuel J. Robé; Feryan Ahmed
Archive | 2009
Yo Matsuo; Yingfu Li; Joel R. Walker; Feryan Ahmed; Ryuji Ohsawa; Shoji Hisada
Archive | 2011
Yusuke Nakamura; Yo Matsuo; Shoji Hisada; Feryan Ahmed; Raymond Huntley; Zohreh Sajjadi-Hashemi; David Jenkins; Robert B. Kargbo; Wenge Cui; Polivina Jolicia F. Gauuan; Joel R. Walker; Helene Decornez; Mahender Gurram