17482-09-6Relevant academic research and scientific papers
Convergent, stereoselective synthesis of the GHIJ fragment of brevetoxin A
Crimmins, Michael T.,Zuccarello, J. Lucas,Cleary, Pamela A.,Parrish, Jonathan D.
, p. 159 - 162 (2007/10/03)
(Chemical Equation Presented) A stereoselective synthesis of the GHIJ fragment of brevetoxin A utilizing a convergent assembly strategy is described. Glycolate alkylation, ring-closing metathesis, and Hosomi-Sakurai reactions were central operations in the construction of the G ring and J ring subunits, which were united through a Horner-Wadsworth-Emmons coupling. Subsequent dehydrative cyclization produced an endocyclic enol ether that was further elaborated to the tetracyclic GHIJ fragment of brevetoxin A.
Improved synthesis of the ABCDE fragment of brevetoxin A
Crimmins, Michael T.,McDougall, Patrick J.,Ellis, J. Michael
, p. 4079 - 4082 (2007/10/03)
A second-generation synthesis of the BCDE fragment of brevetoxin A is described. Novel reactions were developed that extend the utility of the asymmetric glycolate alkylation reaction and improve scale-up to provide gram quantities of the B and E subunits
A convergent coupling strategy for the formation of polycyclic ethers: Stereoselective synthesis of the BCDE fragment of brevetoxin A
Crimmins, Michael T.,McDougall, Patrick J.,Emmitte, Kyle A.
, p. 4033 - 4036 (2007/10/03)
(Chemical Equation Presented) A stereoselective synthesis of the BCDE fragment of brevetoxin A has been completed. anti-Glycolate aldol, glycolate alkylation, and ring-closing metathesis reactions were employed as key bond-forming events. A convergent ass
Synthesis of a Protected C-11/C-17 Segment of Mycinolide-V
Ditrich, Klaus,Hoffmann, Reinhard W.
, p. 15 - 21 (2007/10/02)
Starting from D-ribonolactone, the cyclopentylidene-protected dihydroxy ester 12 was prepared in five steps.Reaction of its enolate 13 with benzyloxymethyl iodide gave the esters 15 and 16 with modest selectivity.Each of these was converted into the desir
