Total Synthesis of Lophirone F Hexamethyl Ether

  • Le, Hoang M.
  • Mac, Hung D.
  • Oh, Chang Ho
  • Do, Dung T.
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초록

A practical and efficient approach for the total synthesis of the (+/-)-lophirone F hexamethyl ether was reported. The compound was synthesized in 8 steps with a 14.6% overall yield. The key features of this synthesis are the stereoselective synthesis of a 2,5-diaryl-3,4-disubstituted tetrahydrofuran skeleton via a sequence of [3+2] cycloaddition/Krapcho decarboxylation and the installation of two aryl ketone groups bypassing potential epimerization of adjacent stereocenters.

키워드

Lophirone F[3+2] CycloadditionKrapcho decarboxylationNatural productsTotal synthesisAMIDE BOND FORMATIONSTEREOSELECTIVE-SYNTHESISENANTIOSELECTIVE SYNTHESIS3+2 CYCLOADDITIONTETRAHYDROFURANSCYCLOPROPANESALDEHYDESACIDROUTES
제목
Total Synthesis of Lophirone F Hexamethyl Ether
저자
Le, Hoang M.Mac, Hung D.Oh, Chang HoDo, Dung T.
DOI
10.1002/ejoc.201801827
발행일
2019-04
유형
Article
저널명
European Journal of Organic Chemistry
2019
13
페이지
2362 ~ 2367