@article {42807,
	title = {Synthesis of C(27){\textendash}C(38) fragment of aflastatin A},
	journal = {Tetrahedron},
	volume = {69},
	year = {2013},
	month = {JAN},
	pages = {1830{\textendash}1840},
	abstract = {<p>Efforts at finding out a strategy for the synthesis of the densely hydroxylated C(27){\textendash}C(48) fragment of aflastatin A have been described. The initial studies dealing with alkyne{\textendash}epoxide coupling using a linear polyol epoxide resulted in a debenzylative cycloetherification leading to a C-arabinoside derivative. This problem has been addressed by applying an epoxide pendant on a furanosyl unit. With the model alkyne, the epoxide{\textendash}alkyne coupling proceeded smoothly. Subsequently, following a sequence of [Pd]-mediated alkynone cycloisomerization/stereoselective hydroboration{\textendash}oxidation, the synthesis of the central C(27){\textendash}C(38) fragment has been executed. When employed, the original C(33){\textendash}C(48) alkyne, the coupling and the cycloisomerizations are facile. However, the resulting glycals are unstable, thus warranting a revision in our approach.</p>},
	keywords = {Aflastatin; Epoxide{\textendash}alkyne coupling; ω-Alkynone cycloisomerization; Palladium catalysis; Hydroboration},
	doi = {10.1016/j.tet.2012.12.065},
	author = {Narute, Sachin B. and Ramana, C.V.}
}
