- Simplified deoxypropionate acyl chains for mycobacterium tuberculosis sulfoglycolipid analogues: Chain length is essential for high antigenicity
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The longer, the better: Increasing the lengths of the 1,3-methyl-branched fatty acyl chain units in mycobacterial diacylated sulfoglycolipid (Acyl 2SGL) analogues led to dramatic improvements in their antigenic properties and gave products more
- Gau, Benjamin,Lemetais, Aurelie,Lepore, Marco,Garcia-Alles, Luis Fernando,Bourdreux, Yann,Mori, Lucia,Gilleron, Martine,De Libero, Gennaro,Puzo, Germain,Beau, Jean-Marie,Prandi, Jacques
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p. 2413 - 2417
(2014/01/06)
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- Enantioselective total synthesis and determination of the absolute configuration of the 4,6,8,10,16,18-hexamethyldocosane from Antitrogus parvulus
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The absolute and relative configuration of the hexamethyldocosane (1) isolated from the cuticula of Antitrogus parvulus was determined based on the total synthesis of both diastereomers 1a and 1b in enantiomerically pure form. The synthesis demonstrates t
- Herber, Christian,Breit, Bernhard
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p. 3512 - 3519
(2008/02/12)
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- Enantioselective total synthesis and determination of the absolute configuration of the 4,6,8,10,16,18-hexamethyldocosane from Antitrogus parvulus
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(Chemical Equation Presented) A copper-catalyzed sp3-sp 3 cross-coupling for fragment coupling in a total synthesis is demonstrated. The diastereo- and enantioselective total synthesis of the 4,6,8,10,16,18-hexamethyldocosanes highli
- Herber, Christian,Breit, Bernhard
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p. 5267 - 5269
(2007/10/03)
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- A NEW PROCESS FOR THE PREPARATION OF EPOTHILONE DERIVATIVES, NEW EPOTHILONE DERIVATIVES AS WELL AS NEW INTERMEDIATE PRODUCTS FOR THE PROCESS AND THE METHODS OF PREPARING SAME
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The present invention provides a synthesis for the preparation of epothilone derivatives of formula (9) wherein R1 is methyl, and R2 has the meaning of an unsubstituted or substituted aryl, an unsubstituted or substituted heteroaryl or an unsubstituted or substituted heterocyclic radical fused to a benzene nucleus, and salts thereof, and intermediates for the synthesis of a compound of formula (9).
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- Radical-induced opening of trisubstituted epoxides: Application in the synthesis of C1-C12 segment of epothilones
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Diastereo- and regioselective opening of a trisubstituted epoxy ketone at the more substituted carbon using samarium(II) iodide presents an alternate approach to the C5-C7 aldol moiety with β-hydroxyketo framework in the stereoselective synthesis of C1-C12 segment of epothilones.
- Chakraborty,Dutta
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p. 101 - 104
(2007/10/03)
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- Synthetic studies of microsclerodermins. A stereoselective synthesis of a core building block for (2S,3R,4S,5S,6S,11E)-3-Amino-6-methyl-12- (4-methoxyphenyl)-2,4,5-trihydroxydodec-11-enoic acid (AMMTD)
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A core building block 3 for (2S,3R,4S,5S,6S,11E)-3-amino-6-methyl-12- (4-methoxyphenyl)-2,4,5-trihydroxydodec-11-enoic acid (2, AMMTD) has been efficiently synthesized using the Sharpless asymmetric dihydroxylation and the Dondoni's furan addition to a ni
- Sasaki, Shigekazu,Hamada, Yasumasa,Shioiri, Takayuki
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p. 3013 - 3016
(2007/10/03)
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- Total synthesis of epothilone A: The macrolactonization approach
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This highly convergent and practical total synthesis of the antitumor agent epothilone A uses a macrolactonization as the key step. The strategy may provide access to a variety of epothilones desirable for biological screening.
- Nicolaou,Sarabia,Ninkovic,Yang
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p. 525 - 527
(2007/10/03)
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- Total syntheses of epothilones A and B via a macrolactonization-based strategy
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The total syntheses of epothilones A (1) and B (2) and several analogues thereof are described. The reported strategy relies on a macrolactonization approach and features selective epoxidation of the macrocycle double bond in precursors 3 and 4 (Scheme 1), respectively, as well as high convergency and flexibility. Building blocks 9-12 and 15 were constructed by asymmetric processes and coupled via Wittig, aldol, and macrolactonization reactions to afford the basic skeleton of epothilones and that of several of their analogues by a relatively short route. The utilization ofintermediate 14, obtained via a stereoselective Wittig reaction and its Enders coupling to SAMP hydrazone 13 (Scheme 8), in combination with a stereoselective aldol reaction with the modified substrate 69 (Scheme 10) improved the stereoselectivity and efficiency of the total synthesis of these new and highly potent microtubule binding antitumor agents.
- Nicolaou,Ninkovic,Sarabia,Vourloumis,He,Vallberg,Finlay,Yang
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p. 7974 - 7991
(2007/10/03)
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