First total synthesis of (+)-indicanone

Organic & Biomolecular Chemistry
Yujiro HayashiChisato Mukai

Abstract

The first total synthesis of the guaiane-type sesquiterpene, (+)-indicanone (1), isolated from the root of Wikstroemia indica, was accomplished based on the rhodium(I)-catalyzed Pauson-Khand-type reaction of the allenyne derivative, which was derived from (+)-limonene. This total synthesis unambiguously confirmed the complete structure of (+)-indicanone involving its absolute stereochemistry.

References

Aug 24, 1999·International Journal of Immunopharmacology·R Manjeet K, B Ghosh
Jan 7, 2005·Chemical & Pharmaceutical Bulletin·Li-Yan WangSusumu Kitanaka
Mar 10, 2006·Organic Letters·Fuyuhiko Inagaki, Chisato Mukai
Dec 29, 2007·The Journal of Organic Chemistry·Toshiyuki HiroseChisato Mukai
Jun 30, 2009·The Journal of Organic Chemistry·Daisuke AburanoChisato Mukai

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Citations

Feb 12, 2014·Chemical Society Reviews·S KitagakiC Mukai
Jun 21, 2018·Natural Product Reports·Kaiqing MaMingji Dai
Jul 26, 2013·Natural Product Reports·Braulio M Fraga
Sep 11, 2012·Organic & Biomolecular Chemistry·Aurélien TapJanick Ardisson
Jul 31, 2014·The Journal of Organic Chemistry·Kosuke FujiokaKozo Shishido

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