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ChemicalBook CAS DataBase List ISO-OSAJIN
5745-54-0

ISO-OSAJIN synthesis

2synthesis methods
-

Yield:5745-54-0 75%

Reaction Conditions:

with acetic acid at 100;

Steps:

6.1 4.6. Synthesis of Isoosajin (14) and isopomiferin (16)

General procedure: Isoosajin (14) and isopomiferin (16) were synthesized by adaptingthe procedure reported by Wolfrom et al. [13]. The reactions werecarried out on the opportune intermediates, which were previouslyisolated from M. pomifera fruits according to a previously reportedprocedure [9]. To perform the cyclization reaction, a round bottomflask was charged with osajin or pomiferin and 7 mL of glacial aceticacid. The mixture was heated to 100 °C and, subsequently, 0.2 mL ofsulfuric acid were added dropwise. The mixture was stirred at roomtemperature and the reaction was monitored by TLC (hexane/ethylacetate 1:1). The reaction was quenched by pouring the mixture in coldwater. The resulting solid was collected by filtration to give the desiredproduct.

References:

Ribaudo, Giovanni;Coghi, Paolo;Zanforlin, Enrico;Law, Betty Yuen Kwan;Wu, Yuki Yu Jun;Han, Yu;Qiu, Alena Congling;Qu, Yuan Qing;Zagotto, Giuseppe;Wong, Vincent Kam Wai [Bioorganic Chemistry,2019,vol. 87,p. 474 - 483]