Total Synthesis of Panaginsene

Singh, VK and Chakraborty, TK (2021) Total Synthesis of Panaginsene. In: Chemistry - An Asian Journal .

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Abstract

The total synthesis of panaginsene has been accomplished in 11 linear steps starting from methyl 3,3-dimethyl-5-oxocyclopent-1-ene-1-carboxylate. The key steps are a Sharpless asymmetric epoxidation and Ti(III)-mediated reductive epoxide opening-radical cyclization to construct the chiral quaternary carbon stereocenter followed by a very challenging HWE olefination reaction on an 1,3-keto aldehyde and a late stage McMurry olefination using low valent titanium to construct the highly constrained angular tetrasubstituted olefin in a five-membered ring. © 2021 Wiley-VCH GmbH

Item Type:	Journal Article
Publication:	Chemistry - An Asian Journal
Publisher:	John Wiley and Sons Ltd
Additional Information:	The copyright for this article belongs to John Wiley and Sons Ltd
Keywords:	Biochemistry; Synthesis (chemical); Titanium compounds, Epoxide openings; Five-membered rings; Low valent titanium; Quaternary carbon; Radical cyclizations; Sharpless asymmetric epoxidations; Tetrasubstituted olefins; Total synthesis, Cyclization
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	29 Mar 2021 07:03
Last Modified:	29 Mar 2021 07:03
URI:	http://eprints.iisc.ac.in/id/eprint/68594

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