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Synthetic Studies of Biomimetic Diels–Alder Processes toward the Helicterin Family of Natural Products
Author(s) -
Snyder Scott A.,
Kontes Ferenc
Publication year - 2011
Publication title -
israel journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.908
H-Index - 54
eISSN - 1869-5868
pISSN - 0021-2148
DOI - 10.1002/ijch.201100004
Subject(s) - chemistry , diels–alder reaction , natural product , natural (archaeology) , core (optical fiber) , alder , organic chemistry , ecology , archaeology , catalysis , materials science , composite material , history , biology
Although the [2.2.2]‐bicyclooctene core of the helicterin, helisorin, and helisterculin class of neolignan natural products could conceivably arise in Nature via Diels–Alder reactions, synthetic explorations have revealed that only under very non‐biomimetic conditions can such cycloadditions be performed. In this article, we provide a personal account of explorations towards this natural product family, sharing some additional unpublished synthetic work to test the viability of an alternate, Diels–Alder‐based, biogenetic hypothesis for the generation of this unique collection of secondary metabolites.