77412-05-6Relevant articles and documents
Total Synthesis of (-)-Lasonolide A
Trost, Barry M.,Stivala, Craig E.,Fandrick, Daniel R.,Hull, Kami L.,Huang, Audris,Poock, Caroline,Kalkofen, Rainer
, p. 11690 - 11701 (2016/10/06)
The lasonolides are novel polyketides that have displayed remarkable biological activity in vitro against a variety of cancer cell lines. Herein we describe our first-generation approach to the formal synthesis of lasonolide A. The key findings from these studies ultimately allowed us to go on and complete a total synthesis of lasonolide A. The convergent approach unites two highly complex fragments utilizing a Ru-catalyzed alkene-alkyne coupling. This type of coupling typically generates branched products; however, through a detailed investigation, we are now able to demonstrate that subtle structural changes to the substrates can alter the selectivity to favor the formation of the linear product. The synthesis of the fragments features a number of atom-economical transformations which are highlighted by the discovery of an engineered enzyme to perform a dynamic kinetic reduction of a β-ketoester to establish the absolute stereochemistry of the southern tetrahydropyran ring with high levels of enantioselectivity.
Enantioselective total synthesis of macrolide antitumor agent (-)-lasonolide A
Ghosh, Arun K.,Gong, Gangli
, p. 1437 - 1440 (2008/02/03)
Equation presented An enantioselective total synthesis of (-)-lasonolide A is described. The upper tetrahydropyran ring was constructed stereoselectively by an intramolecular 1,3-dipolar cycloaddition reaction. The bicyclic isooxazoline led to the tetrahy
Lasonolide A: Structural revision and total synthesis
Song, Ho Young,Joo, Jung Min,Kang, Jung Won,Kim, Dae-Shik,Jung, Cheol-Kyu,Kwak, Hyo Shin,Park, Jin Hyun,Lee, Eun,Hong, Chang Yong,Jeong, ShinWu,Jeon, Kiwan
, p. 8080 - 8087 (2007/10/03)
The proposed structure of lasonolide A was synthesized employing radical cyclization reactions of β-alkoxyacrylates for preparation of the tetrahydropyranyl units A and B, but the spectroscopic data did not match those of the natural product. Both enantio