330150-89-5Relevant academic research and scientific papers
18O assisted analysis of a γ,δ-epoxyketone cyclization: Synthesis of the C16-C28 fragment of ammocidin D
Chau, Stephen T.,Hayakawa, Yoichi,Sulikowski, Gary A.
supporting information; experimental part, p. 756 - 759 (2011/04/24)
The C16-C28 fragment common to the cytotoxic macrolide ammocidin D has been prepared by a stereospecific 5-exo closure of a γ,δ-epoxyketone followed by a rearrangement to a pyran acetal. The reaction pathway was traced by 18O labeling of the ke
Stereochemistry of sphinxolides and reidispongiolides. Asymmetric synthesis of the C17-C22 fragment of reidispongiolide A
Zampella, Angela,Bassarello, Carla,Bifulco, Giuseppe,Gomez-Paloma, Luigi,D'Auria, Maria Valeria
, p. 785 - 790 (2007/10/03)
Five fragments, 2a-4b, embedding all the stereogenic centers of reidispongiolide A (1), have been prepared by a controlled ozonolysis of the natural compound. The absolute stereochemistry of the asymmetric centers of fragment 3, corresponding to the C17-C22 portion of reidispongiolide A, was determined by enantioselective synthesis and application of the advanced Mosher method.
Stereochemical studies on sphinxolide: Advances in the J-based NMR determination of the relative configuration of flexible systems
Bassarello, Carla,Bifulco, Giuseppe,Zampella, Angela,D'Auria, Maria Valeria,Riccio, Raffaele,Gomez-Paloma, Luigi
, p. 39 - 44 (2007/10/03)
An improved version of the J-based NMR configurational analysis of flexible organic molecules, that relies on extensive use of HSQC-TOCSY spectra, was applied to the stereochemical study of sphinxolide, a potent anti-tumor marine macrolide acting on cell microfilaments that has lately proven to circumvent multi-drug-resistance (MDR) in cancer cells. NMR data allowed stereochemical assignment of all molecular segments except the C18-C19 unit, whose configuration had to be addressed by a chemical/degradative approach.
