393530-60-4Relevant articles and documents
Ambruticins: tetrahydropyran ring formation and total synthesis
Bowen, James I.,Crump, Matthew P.,Wang, Luoyi,Willis, Christine L.
, p. 6210 - 6215 (2021/07/28)
The ambruticins are a family of polyketide natural products which exhibit potent antifungal activity. Gene knockout experiments are in accord with the proposal that the tetrahydropyran ring of the ambruticins is formedviathe AmbJ catalysed epoxidation of the unsaturated 3,5-dihydroxy acid, ambruticin J, followed by regioselective cyclisation to ambruticin F. Herein, a convergent approach to the total synthesis of ambruticin J is described as well as model studies involving epoxidation and cyclisations of unsaturated hydroxy esters to give tetrahydropyrans and tetrahydrofurans. The total synthesis involves preparation of three key fragments which were unitedviaa Suzuki-Miyaura cross-coupling and Julia-Kocienski olefination to generate the required carbon framework. Global deprotection to a triol and selective oxidation of the primary alcohol gave, after hydrolysis of the lactone, ambruticin J.
Total synthesis of (+)-ambruticin S: Probing the pharmacophoric subunit
Hanessian, Stephen,Focken, Thilo,Mi, Xueling,Oza, Rupal,Chen, Bin,Ritson, Dougal,Beaudegnies, Renaud
experimental part, p. 5601 - 5618 (2010/11/03)
An enantioselective synthesis of the antifungal natural product (+)-ambruticin S has been accomplished starting with the readily available methyl α-d-glucopyranoside, (R)-Roche ester, and (S)-glycidol as chirons, which encompassed seven of the 10 stereogenic centers of the target molecule. The remaining three centers were set by a highly diastereoselective, asymmetric cyclopropanation employing a chiral, nonracemic phosphonamide reagent. Our strategy for the construction of the dihydropyran subunit involved a highly syn-selective Lewis acid catalyzed 6-endo-trig cyclization. Other key steps in the synthesis featured an epoxide opening with a dithiane anion, two efficient phosphonamide-anion based olefinations, and a late-stage C-glycosylation.
A short synthesis of the common dihydropyran segment of the antifungal agents ambruticin and jerangolid A
Lukesh, Julie M.,Donaldson, William A.
, p. 5529 - 5531 (2007/10/03)
The dihydropyranyl segment common to ambruticin and jerangolid A was prepared in six steps (31.7% yield) from (S)-2-benzyloxypropanal via silyloxydiene cyclocondensation, followed by C-glycosidation, and eventual epimerization at C18.
