- A facile approach for the synthesis of C13-C24 fragments of maltepolides A, C and D
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A linear, chiron approach for the synthesis of C13-C24 fragments of cytostatic maltepolides A, C and D consisting of a tetrahydrofuran subunit and a chiral alkenyl/alkyl substituent is achieved from (+)-diethyl l-tartrate. The other chiral stereocenters were generated by employing key reactions such as Crimmins aldol, alkynylation and CeCl3·7H2O mediated Luche reduction reactions.
- Rao, P. Sankara,Srihari
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p. 9629 - 9638
(2016/10/22)
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- Enantioselective Synthesis and Biological Activity of (3S,4R)- and (3S,4S)-3-Hydroxy-4-hydroxymethyl-4-butanolides in Relation to PGE2
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Compounds 9 and 13 were synthesized, and their structures and stereochemistry were elucidated by spectroscopic methods. In competition binding experiments, specific [3H]-PGE2 binding was significantly displaced by compound 9 and, to a lesser extent, by 13, in a dose-dependent manner. The biological properties of compound 9 were studied on HL-60 cells, and several effects were found related to those of PGE 2. Compound 9 increases c-fos mRNA level as does PGE2 and antagonizes TPA-induced terminal differentiation.
- Miranda, Pedro O.,Estévez, Francisco,Quintana, José,Garcia, Candelaria I.,Brouard, Ignacio,Padrón, Juan I.,Pivel, Juan P.,Bermejo, Jaime
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p. 292 - 295
(2007/10/03)
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- An enantioselective synthesis of the C1-C9 segment of antitumor macrolide peloruside A
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A stereocontrolled synthesis of the C1-C9 segment of the marine natural product peloruside A is described. The key steps involve Sharpless's catalytic asymmetric dihydroxylation reaction, a chelation-controlled reduction of chiral β-alkoxy ketones to elaborate the syn-1,3-diol functionality and a ring-closing olefin metathesis of a homoallylic alcohol-derived acrylate ester to form an α,β-unsaturated δ-lactone.
- Ghosh, Arun K.,Kim, Jae-Hun
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p. 3967 - 3969
(2007/10/03)
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