- Convergent stereospecific total synthesis of monocillin I and radicicol: Some simplifications and improvements
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A much improved and reliable access to the macrolide 9, key-intermediate in our synthesis of monocillin I and radicicol is reported, via a modification of our first synthesis. The formation of the conjugated E,Z-dienone trans-epoxide is now achieved in a much higher yield, in a stereospecific reaction, by elimination of the methanesulfonate ester of the 6′-OH of the intermediate macrolide. It is also shown that the configuration of the 6′-OH has no significant incidence on all the steps leading to 9, and that consequently the two diastereoisomers 12, epimeric at 6′, can be used for the synthesis of radicicol.
- Tichkowsky, Isabelle,Lett, Robert
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- Halohydrin and oxime derivatives of radicicol: Synthesis and antitumor activities
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Novel halohydrin and oxime derivatives of radicicol (1) were prepared and evaluated for their v-src tyrosine kinase inhibitory, antiproliferative, and antitumor activities. Some of the resulting derivatives showed significantly improved antitumor activities than those of 1 in vitro as tested in a cell proliferation assay and in vivo using sc-inoculated human breast carcinoma and epidermoid tumor models. Design and synthesis of radicicol-based novel affinity probes are also described.
- Agatsuma, Tsutomu,Ogawa, Harumi,Akasaka, Kazuhito,Asai, Akira,Yamashita, Yoshinori,Mizukami, Tamio,Akinaga, Shiro,Saitoh, Yutaka
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- Synthesis and structure-activity relationships of radicicol derivatives and WNT-5A expression inhibitory activity
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WNT-5A, a secretory glycoprotein, is related to the proliferation of dermal papilla cells. To develop a hair-growth stimulant, we have been searching for inhibitors of WNT-5A expression. We identified radicicol (1) as an active compound, and synthesized s
- Shinonaga, Hideki,Noguchi, Toshiya,Ikeda, Akiko,Aoki, Mari,Fujimoto, Natsuko,Kawashima, Akira
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p. 4622 - 4635
(2009/10/23)
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- Solution- and solid-phase synthesis of radicicol (monorden) and pochonin C
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A modular synthesis for pochonin C and radicicol is reported. The two natural products were prepared in seven and eight steps, respectively, from three readily available fragments. Alternative syntheses of these compounds were achieved using a combination of polymer-bound reagents and solid phase reactions. The conformation of the two natural products was studied and compared by using 2D NMR spectroscopy.
- Barluenga, Sofia,Moulin, Emilie,Lopez, Pilar,Winssinger, Nicolas
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p. 4935 - 4952
(2007/10/03)
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- Modular asymmetric synthesis of pochonin C
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Back to its origins: Pochonin C was synthesized in 11 steps from the four fragments shown in the scheme. This asymmetric synthesis and the conversion of pochonin C into radicicol defines the configuration at the center bearing the chlorine atom as S. lpc
- Barluenga, Sofia,Lopez, Pilar,Moulin, Emilie,Winssinger, Nicolas
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p. 3467 - 3470
(2007/10/03)
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- Concise asymmetric syntheses of radicicol and monocillin I
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Radicicol (1) exhibits potent anticancer properties in vitro, which are likely to be mediated through its high affinity (20 nM) for the molecular chaperone Hsp90. Recently, we reported the results of a synthetic program targeting radicicol (1) and monocil
- Garbaccio,Stachel,Baeschlin,Danishefsky
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p. 10903 - 10908
(2007/10/03)
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- Convergent stereospecific total synthesis of Monocillin I and Monorden (or Radicicol)
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The first total syntheses of the antifungal resorcylic macrolides Monocillin I and Monorden (or Radicicol) have been achieved by a convergent stereospecific route. TBDMS phenol ethers were found to be suitable for all the scheme and were removed in the ul
- Lampilas,Lett
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p. 777 - 780
(2007/10/02)
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