A Stereoconvergent Intramolecular Diels–Alder Cycloaddition Related to the Construction of the Decalin Core of neo-Clerodane Diterpenoids

A Stereoconvergent Intramolecular Diels–Alder Cycloaddition Related to the Construction of the Decalin Core of neo-Clerodane Diterpenoids

Several examples of a highly specific, stereoconvergent intramolecular Diels–Alder cycloaddition that led to the trans-decalin core of neo-clerodane diterpenoids are described. The relative configuration adjacent to the dienophile, which led to C4 of the decalin system, as well as the electron-withd...

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Veröffentlicht in:Journal of organic chemistry 2013-04, Vol.78 (8), p.3895-3907
Hauptverfasser: Butler, Sean C, Forsyth, Craig J
Format: Artikel
Sprache:eng
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Cycloaddition Reaction
Diterpenes - chemistry
Diterpenes, Clerodane - chemistry
Molecular Conformation
Molecular Structure
Stereoisomerism
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Forsyth, Craig J
description Several examples of a highly specific, stereoconvergent intramolecular Diels–Alder cycloaddition that led to the trans-decalin core of neo-clerodane diterpenoids are described. The relative configuration adjacent to the dienophile, which led to C4 of the decalin system, as well as the electron-withdrawing effects of various substituents and conformational rigidity of the Diels–Alder precursors were explored.
doi_str_mv 10.1021/jo400029u
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subjects Cycloaddition Reaction
Diterpenes - chemistry
Diterpenes, Clerodane - chemistry
Molecular Conformation
Molecular Structure
Stereoisomerism
title A Stereoconvergent Intramolecular Diels–Alder Cycloaddition Related to the Construction of the Decalin Core of neo-Clerodane Diterpenoids
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