- New approach for the stereoselective synthesis of (+)-epi-cytoxazone
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The stereoselective total synthesis of (+)-epi-cytoxazone was performed satisfactorily in 8 steps, in 17percent overall yield, via a novel route from 2,3-O-(3-pentylidene)-(R)-glyceraldehyde. The bulky group alkene-ketal allowed intramolecular control of
- Miranda, Izabel L.,Sartori, Suélen K.,Diaz, Marisa A.N.,Diaz-Mu?oz, Gaspar
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p. 585 - 591
(2019/08/26)
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- Modifications of C-2 on the pyrroloquinoline template aimed at the development of potent herpesvirus antivirals with improved aqueous solubility
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A series of C-2 pyrroloquinoline analogs designed to improve aqueous solubility were examined for herpesvirus polymerase and antiviral activity. Several analogs were identified that maintained the antiviral activity of the previous development candidate against HCMV, HSV-1 and VZV, but with significantly improved aqueous solubility.
- Nieman, James A.,Nair, Sajiv K.,Heasley, Steven E.,Schultz, Brenda L.,Zerth, Herbert M.,Nugent, Richard A.,Chen, Ke,Stephanski, Kevin J.,Hopkins, Todd A.,Knechtel, Mary L.,Oien, Nancee L.,Wieber, Janet L.,Wathen, Michael W.
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supporting information; experimental part
p. 3039 - 3042
(2010/07/03)
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- Synthetic studies toward amphidinolide A: Synthesis of fully functionalized subunits
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A retrosynthetic breakdown of amphidinolide A affords four fragments A- D and illustrates the main synthetic challenges of this molecule. A concise stereoselective synthesis of the four appropriately functionalized subtargets is described.
- Terrell, Lamont R.,Ward III, Joseph S.,Maleczka Jr., Robert E.
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p. 3097 - 3100
(2007/10/03)
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- 2,3-O-(3-pentylidene)-D-glyceraldehyde and 2,3-O-(3-pentylidene)-L-glyceraldehyde: Convenient glyceraldehyde surrogates obtained via a novel periodate-based oxidation system
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The synthesis of two novel glyceraldehyde surrogates, 2,3-O-(3-pentylidene)-D-glyceraldehyde (2) and 2,3-O-(3-pentylidene)-L-glyceraldehyde (3) is presented. Synthesis, handling and storage advantages of 2 and 3 over the conventionally employed 2,3-O-isopropylidene-D-glyceraldehyde (1) are discussed. The 3-pentanone-derived protecting group facilitates the extraction of product from aqueous oxidation solutions, while the 3-pentanone liberated on ketal deprotection can be efficiently removed at reduced pressures. The synthesis employs a buffered potassium periodate oxidation which offers significant advantages over sodium periodate in glycol cleavage reactions.
- Schmid,Bradley
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p. 587 - 590
(2007/10/02)
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