68930-68-7Relevant articles and documents
A diastereoselective oxa-pictet-spengler-based strategy for (+)-frenolicin B and epi -(+)-frenolicin B synthesis
Zhang, Yinan,Wang, Xiachang,Sunkara, Manjula,Ye, Qing,Ponomereva, Larissa V.,She, Qing-Bai,Morris, Andrew J.,Thorson, Jon S.
, p. 5566 - 5569 (2013)
An efficient diastereoselective oxa-Pictet-Spengler reaction strategy was developed to construct benzoisochroman diastereomers. The utility of the reaction was demonstrated in the context of both the total synthesis of naturally occurring pyranonaphthoquinones (+)-frenolicin B and epi-(+)-frenolicin B as well as a range of frenolicin precursor analogs. The method is versatile and offers exquisite stereocontrol and, as such, offers a synthetic advance for the synthesis of pyranonaphthoquinone analogs.
A chiron approach to the total synthesis of (-)-juglomycin A, (+)-kalafungin, (+)-frenolicin B, and (+)-deoxyfrenolicin
Fernandes, Rodney A.,Chavan, Vijay P.,Mulay, Sandip V.,Manchoju, Amarender
, p. 10455 - 10460 (2013/01/15)
A general, efficient, and common strategy for the synthesis of (-)-juglomycin A, (+)-kalafungin, (+)-frenolicin B, and (+)-deoxyfrenolicin is reported here. The strategy involves the synthesis of a key building block alkyne from a cheap chiral pool material, d-glucono-δ-lactone, Doetz benzannulation, oxa-Pictet-Spengler reaction, and H2SO 4-mediated epimerization.
Direct Total Syntheses of Frenolicin B and Kalafungin via Highly Regioselective Diels-Alder Reactions
Kraus, George A.,Li, Jun,Gordon, Mark S.,Jensen, Jan H.
, p. 1154 - 1159 (2007/10/02)
Frenolicin B, an anticoccidial agent, has been synthesizes in six steps from ketone 3.Racemic kalafungin, an antifungal agent, has been synthesized in five steps.The key step in both syntheses, a regioselective Diels-Alder reaction, proceeds with complete