Studies directed toward the synthesis of hedycoropyrans: total synthesis of des-hydroxy (−)-hedycoropyran B (-rhoiptelol B)

A full account of our efforts directed towards the synthesis of the diarylheptanoid-derived natural products hedycoropyrans that led to the total synthesis of ent -rhoiptelol B is described. In this endeavor, we have attempted two distinct synthetic strategies to access hedycoropyrans A and B, which...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2022-01, Vol.2 (2), p.444-463
Main Authors: Kataria, Priyanka, Nomula, Rajesh, Kontham, Ravindar
Format: Article
Language:English
Subjects:
Epoxidation
Michael reaction
Natural products
Synthesis
Vanillin
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Summary:A full account of our efforts directed towards the synthesis of the diarylheptanoid-derived natural products hedycoropyrans that led to the total synthesis of ent -rhoiptelol B is described. In this endeavor, we have attempted two distinct synthetic strategies to access hedycoropyrans A and B, which led us to establish a facile synthetic route for des-hydroxy (−)-hedycoropyran B ( ent -rhoiptelol B) from simple and readily accessible building blocks of 4-allylanisole and vanillin, employing Sharpless asymmetric epoxidation, CBS reduction, and an intramolecular AgOTf-catalyzed oxa-Michael reaction of suitably functionalized hydroxy-ynone as key transformations. The investigations disclosed herein will provide insights into designing novel synthetic routes for THP-DAH-derived natural products. Studies directed towards the stereoselective synthesis of the diarylheptanoid-derived natural products hedycoropyrans leading to the total synthesis of (−)-hedycoropyran B ( ent -rhoiptelol B) are presented.
ISSN:1477-0520
1477-0539
DOI:10.1039/d1ob01972d