Issue 2, 2022

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

Abstract

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.

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

Supplementary files

Article information

Article type
Paper
Submitted
08 Oct 2021
Accepted
01 Dec 2021
First published
02 Dec 2021

Org. Biomol. Chem., 2022,20, 444-463

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

P. Kataria, R. Nomula and R. Kontham, Org. Biomol. Chem., 2022, 20, 444 DOI: 10.1039/D1OB01972D

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