Application of Cp2 TiCl-Promoted Radical Cyclization: A Unified Strategy for the Syntheses of Iridoid Monoterpenes

The Journal of Organic Chemistry
Hina P A KhanTushar Kanti Chakraborty

Abstract

An expedient approach toward the unified total syntheses of (+)-iridomyrmecin, (-)-isoiridomyrmecin, (+)-7- epi-boschnialactone, (+)-teucriumlactone, and (-)-dolichodial in chirally pure forms starting from readily available (+)-β-citronellene is delineated combining step economy and simplicity. Highlights include a Ti(III)-mediated reductive epoxide opening-cyclization for the construction of the core cyclopenta[ c]pyran skeleton of the iridoid lactones with complete diastereoselectivity for the newly created bridgehead stereogenic centers. Subsequent transformations facilitate a short access to (+)-teucriumlactone and (-)-dolichodial and formal access to potentially other iridoids.

References

Feb 3, 2007·Chemical & Pharmaceutical Bulletin·Biswanath DindaYoshihiro Harigaya
May 3, 2007·Chemical & Pharmaceutical Bulletin·Biswanath DindaYoshihiro Harigaya
May 14, 2008·Mini Reviews in Medicinal Chemistry·Rosa TundisFrancesco Menichini
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Nov 1, 1980·Journal of Natural Products·L J El-Naggar, J L Beal
May 9, 2014·Organic Letters·Dipendu DasTushar Kanti Chakraborty

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Citations

Oct 6, 2020·Chemistry, an Asian Journal·Ryuji Kouda, Fumika Yakushiji
Aug 3, 2021·The Journal of Organic Chemistry·Sabnam Begum, Tushar Kanti Chakraborty
May 30, 2020·The Journal of Organic Chemistry·Hina P A Khan, Tushar Kanti Chakraborty
Dec 4, 2019·The Journal of Organic Chemistry·Jothi Lakshmi Nallasivam, Tushar Kanti Chakraborty

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