Enantioselective Total Synthesis of 3-Ladderanol through Late-Stage Organocatalytic Desymmetrization**

Ray, S and Mondal, S and Mukherjee, S (2022) Enantioselective Total Synthesis of 3-Ladderanol through Late-Stage Organocatalytic Desymmetrization**. In: Angewandte Chemie - International Edition .

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Abstract

Ladderane phospholipids, with their unusual ladder-like arrangement of concatenated cyclobutane rings, represent an architecturally unique class of natural products. However, despite their fascinating structure and other necessary impetus, only a few synthetic studies of these molecules have been reported so far. We have now devised a concise total synthesis of 3-ladderanol, a component of natural ladderane phospholipids, using an organocatalytic enantioselective desymmetrizing formal C(sp2)- H alkylation. Our synthetic strategy rests on the late-stage introduction of chirality, thus allowing facile access to both enantiomers of 3-ladderanol as well as an analogue. This is the first time a desymmetrization strategy is applied to the synthesis of 3-ladderanol. The scope of this desymmetrizing C(sp2)- H alkylation of meso-cyclobutane-fused cyclohexenediones is also presented. © 2022 Wiley-VCH GmbH.

Item Type:	Journal Article
Publication:	Angewandte Chemie - International Edition
Publisher:	John Wiley and Sons Inc
Additional Information:	The copyright for this article belongs to John Wiley and Sons Inc
Keywords:	Alkylation; Enantioselectivity; Stereochemistry; Synthesis (chemical), Cyclobutane ring; Desym-metrization; Enantioselective total synthesis; Fused-ring system; Ladderane; Late stage; Natural products; Organocatalytic; Synthetic study; Total synthesis, Phospholipids
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	18 May 2022 06:13
Last Modified:	18 May 2022 06:13
URI:	https://eprints.iisc.ac.in/id/eprint/71811

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