39252-69-2Relevant articles and documents
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Zaki
, p. 2269,2271 (1930)
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Total synthesis of enigmazole a from cinachyrella enigmatica. Bidirectional bond constructions with an ambident 2,4-disubstituted oxazole synthon
Skepper, Colin K.,Quach, Tim,Molinski, Tadeusz F.
supporting information; experimental part, p. 10286 - 10292 (2010/09/06)
The first total synthesis of the cytotoxic marine macrolide enigmazole A has been completed in 22 steps (longest linear sequence). The sensitive, densely functionalized 2,4-disubstituted oxazole fragment was constructed using an efficient Negishi-type cou
β-Functionalised radicals in organic synthesis: 2-Acyloxyalkyl radicals from 2-acyloxyalkyl iodides by the tin route
Foubelo, Francisco,Lloret, Francisco,Yus, Miguel
, p. 5131 - 5138 (2007/10/02)
The reaction of iodoesters 1a-c with electrophilic olefins 2a-d and in situ generated tributyltin hydride (from a substoichiometric amount of tributyltin chloride and an excess of sodium borohydride) in the presence of a catalytic amound of AIBN in ethanol at 0 to 20°C yields the expected coupling products 3aa-3cd. Products 4 resulting from an iodine/hydrogen exchange are also obtained as by-products in variable amounts. The stereochemistry of the coupling reaction is studied: starting from trans-2-iodocyclohexyl acetate (1d) and methyl acrylate (2a) a 1/3 mixture of the corresponding cis/trans diastereoisomers is obtained. This result indicates that the corresponding radical coupling is not stereospecific.