292073-45-1Relevant articles and documents
Towards the synthesis of the 4,19-diol derivative of (-)-mycothiazole: Synthesis of a potential key intermediate
Batt, Frederic,Fache, Fabienne
, p. 6039 - 6055 (2011/12/15)
The synthesis of a potential key intermediate for the synthesis of the 4,19-diol derivative of (-)-mycothiazole using convergent strategies is described in this paper. Several approaches have been tested, including cross metathesis and a Julia-Kocienski olefination. Finally, the formation of the 1,1-dialkyl-1,2-ethanediol motif through C4-C5 bond construction was realized by nucleophilic addition of a vinyl iodide derivative to a keto ester after halogen/lithium exchange followed by reduction of the resulting hydroxy ester. The synthesis of the allylic 1,1-dialkyl-1,2-ethanediol group, achieved by halogen/metal exchange followed by addition to aα-keto ester, is the key step of this convergent strategy towards a potential intermediate of mycothiazole-4,19-diol.
Asymmetric total synthesis of (-)-mycothiazole.
Sugiyama,Yokokawa,Shioiri
, p. 2149 - 2152 (2007/10/03)
[structure: see text] In this Letter we describe the first total synthesis of mycothiazole, a polyketide thiazole from a marine sponge. Key steps include our CMD oxidation for the conversion of thiazolidine 11 to thiazole 12 and the Nagao acetate aldol re
