292073-56-4Relevant academic research and scientific papers
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.
Mycothiazole: Synthesis of the C8-C18 subunit and further evidence of the (Z)-Δ14 double bond configuration
Rega, Miriam,Candal, Paloma,Jimenez, Carlos,Rodriguez, Jaime
, p. 934 - 942 (2008/02/13)
The synthesis of mycothiazole derivatives was undertaken in order to have further evidence of the C14-C15 double bond configuration. The recently revised (Z) configuration in the natural compound is consistent with the data found for our synthetic analogs
Total synthesis of mycothiazole, a polyketide heterocycle from marine sponges
Sugiyama, Hideyuki,Yokokawa, Fumiaki,Shioiri, Takayuki
, p. 6579 - 6593 (2007/10/03)
Mycothiazole isolated from marine sponges has been efficiently synthesized in a convergent manner. The key reactions involve the thiazole synthesis by dehydrogenation of the thiazolidine with chemical manganese dioxide (CMD), the Stille coupling, and the Nagao asymmetric acetate aldol reaction using the chiral 1,3-thiazolidine-2-thione. This synthesis clearly established the absolute configuration of natural mycothiazole to be (R).
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
