Total Synthesis of Notoryne

The Journal of Organic Chemistry
Sibadatta SenapatiChepuri V Ramana

Abstract

The structure of notoryne comprises a halogenated 2,2'-bifuranyl moiety along with a terminal cis-enyne unit. In this work, we document the first total synthesis of notoryne, confirming its assigned relative and absolute configurations. The devised route comprises a glucose diacetonide-derived chiral pool intermediate as the starting point and 5- endo bromo-etherification for making the key bis-furan unit, anomeric C-allylation, as well as a relay cross-metathesis to install the cis-enyne unit.

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Citations

Feb 7, 2020·Natural Product Reports·Anthony R CarrollMichèle R Prinsep
Sep 24, 2020·Organic & Biomolecular Chemistry·Rodney A FernandesRamdas S Pathare
May 6, 2021·Organic & Biomolecular Chemistry·Sibadatta Senapati, Chepuri V Ramana
Sep 29, 2019·Journal of the American Chemical Society·Hau Sun Sam ChanJonathan W Burton
Apr 13, 2019·The Journal of Organic Chemistry·Erin D ShepherdRobert S Paton
Oct 13, 2020·ACS Omega·Venkannababu MullapudiChepuri V Ramana

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