1176252-19-9Relevant academic research and scientific papers
Total Synthesis of the Oxopolyene Macrolide (-)-Marinisporolide C
Dias, Luiz C.,De Lucca, Emílio C.
, p. 6278 - 6281 (2015)
The first total synthesis of (-)-marinisporolide C was performed in 25 steps (longest linear sequence) and an overall yield of 1%. Due to the high degree of convergence and robustness, the C9-C35 fragment that corresponds to the polyol portion was obtaine
Total Synthesis of (-)-Marinisporolide C
Dias, Luiz C.,De Lucca, Emilio C.
, p. 3019 - 3045 (2017)
The first total synthesis of (-)-marinisporolide C is described, which establishes unequivocally the relative and absolute configuration of this oxopolyene macrolide. Key features of this synthesis include a series of highly stereoselective aldol reactions followed by directed reductions to build the polyol domain, a Stille cross-coupling reaction to assemble the polyene, and an intramolecular Horner-Wadsworth-Emmons olefination to forge the macrocyclic ring. Despite the initial approach to marinisporolide A using a Yamaguchi macrolactonization reaction that was unsuccessful due to steric hindrance of the oxygen at the C33 position, we were able to prepare a known derivative of marinisporolide A and consequently confirm its stereochemical assignment.
The total synthesis of (-)-cryptocaryol A
Dias,Kuroishi,De Lucca
, p. 3575 - 3584 (2015/03/30)
A stereoselective total synthesis of (-)-cryptocaryol A (1) is described. Key features of the 17-step route include the use of three boron-mediated aldol reaction-reduction sequences to control all stereocenters and an Ando modification of the Horner-Wadsworth-Emmons olefination that permitted the installation of the Z double bond of the α-pyrone ring.
Synthesis of hyacinthacine B3 and purported hyacinthacine B 7
Au, Christopher W. G.,Nash, Robert J.,Pyne, Stephen G.
supporting information; experimental part, p. 713 - 715 (2010/06/12)
The synthesis of hyacinthacines B3 and B7 has confirmed the structure of the former alkaloid and shown that the structure of the latter is incorrect.
Divergent syntheses of resorcylic acid lactones: L-783277, LL-Z1640-2, and hypothemycin
Dakas, Pierre-Yves,Jogireddy, Rajamalleswaramma,Valot, Gaelle,Barluenga, Sofia,Winssinger, Nicolas
supporting information; experimental part, p. 11490 - 11497 (2010/04/28)
The resorcylic acid lactones (RAL) are endowed with diverse biological activity ranging from transcription factor modulators (zearalenone and zearalenol) to HSP90 inhibitors (radicicol and pochonin D) and reversible (aigialomycin D) as well as irreversibl
