103929-83-5Relevant articles and documents
Synthesis of the spiroketal core of integramycin
Prusov, Evgeny V.
, p. 2446 - 2450 (2013)
A concise synthetic strategy towards the spiroketal core of the HIV-integrase inhibitor integramycin (1) was developed. The required ketone precursor was efficiently constructed from two simple and easily accessible subunits by means of a hydrozirconation/copper catalyzed acylation reaction. The effects of different protecting groups on the spiroketalization step were also investigated.
Scalable Total Synthesis of Piceatannol-3′-O-β-d-glucopyranoside and the 4′-Methoxy Congener Thereof: An Early Stage Glycosylation Strategy
Chen, Lei,Li, Jianfeng,Wang, Xiaoting,Zhang, Rong-Ping
, (2021/11/04)
Scalable syntheses of piceatannol-3'-O-β-D-glucopyranoside and the 4'-methoxy congener thereof were achieved. This route features an early implemented Fischer-like glycosylation reaction, a regioselective iodination of phenolic glycoside under strongly acidic conditions, a highly telescoped route to access the styrene derivative, and a key Mizoroki.Heck reaction to render the desired coupled products in high overall yield.
Unexpected O-alkylation and ester migration in phenolic 2,3-diaryl-2,3-dihydrobenzo[b]furans
Tran, Henry,Dickson, Benjamin D.,Barker, David
, p. 2093 - 2096 (2013/04/23)
O-alkylation of 2-(4-methoxyphenyl)-5-hydroxy-3-[1,3-phenylene-bis(4- nitrobenzoate)]-2,3-dihydrobenzo[b]furan results in the unexpected hydrolysis of the nitrobenzoate esters, transfer of a 4-nitrobenzoic acid group to the 5-hydroxyl group and double alkylation of the newly formed 3,5-diphenol moiety. A range of alkyl halides can be used and give access to O-alkyl analogues of -viniferin.
