169105-68-4Relevant articles and documents
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.
Synthesis of (+)-siphonarienone: Asymmetric alkylation using a chiral benzopyrano-isoxazolidine auxiliary
Abiko, Atsushi,Masamune, Satoru
, p. 1081 - 1084 (2007/10/03)
Asymmetric alkylation of the potassium enolates derived from N-propionyl benzopyrano[4,3-c]-isoxazolidine derivatives with chiral alkyl triflates proceeded smoothly with high diastereoselectivity. The stereochemistry of the newly formed stereogenic center was fully controlled by the facial selectivity of the enolate according to the rule of double asymmetric synthesis. The application of this methodology led to the first synthesis of (+)-siphonarienone, a marine polypropionate natural product.
Siloxanes: Versatile Templates for Acyclic Stereocontrol. Synthesis of the C27-C33 Segment of Rapamycin
Hale, Michael R.,Hoveyda, Amir H.
, p. 1643 - 1645 (2007/10/02)
Five-membered siloxane rings may be employed to relay asymmetry along an acyclic chain in an efficient manner.Application of this method to the synthesis of the C27-C33 segment of the immunosuppressant rapamycin is reported.