754239-31-1Relevant academic research and scientific papers
Synthetic study of thermolides: Stereoselective construction of the C10-C21 fragment
Yoshimura, Hikaru,Ishihara, Jun,Hatakeyama, Susumi
, p. 702 - 707 (2019/04/26)
The C10-C21 fragment of nematocidal thermolides, macrocyclic PKS-NRPS hybrid metabolites isolated from a thermophilic fungus, was prepared in a highly stereoselective manner. The stereocontrol was accomplished by taking advantage of a cinchona alkaloid-catalyzed Morita-Baylis-Hillman reaction followed by diastereoselective hydrogenation and a cinchona alkaloid-catalyzed asymmetric β-lactone formation.
Application of the Doetz reaction to construction of a major portion of the ansa macrocycle (-)-kendomycin
White, James D.,Smits, Helmars
, p. 235 - 238 (2007/10/03)
(Chemical Equation Presented) A Doetz reaction employing a terminal alkyne and a Fischer-type alkenylchromium carbenoid led to a pentasubstituted benzene from which a major portion of the Streptomyces metabolite (-)-kendomycin was synthesized.
Total synthesis and biological evaluation of (+)-kalkitoxin, a cytotoxic metabolite of the cyanobacterium Lyngbya majuscula
White, James D.,Xu, Qing,Lee, Chang-Sun,Valeriote, Frederick A.
, p. 2092 - 2102 (2007/10/03)
(+)-Kalkitoxin, a metabolite of the marine cyanobacterium Lyngbya majuscula, was synthesized from (R)-2-methylbutyric acid, (R)-cysteine, and (3S, 4S, 6S)-3,4,6-trimethyl-8-(methylamino)octanoic acid. A key step in the synthesis was installation of the anti,anti methyl stereotriad by means of a tandem asymmetric conjugate addition of an organocopper species to an α,β-unsaturated N-acyl oxazolidin-2-one followed in situ by α-methylation of the resultant enolate. The thiazoline portion of kalkitoxin was assembled by titanium tetrachloride catalyzed cyclization of a vinyl substituted amido thiol.
