Meroterpenoid total synthesis: conversion of geraniol and farnesol into
amorphastilbol, grifolin and grifolic acid by dioxinone-β-keto-acylation,
palladium catalyzed decarboxylative allylic rearrangement and aromatization
amorphastilbol, grifolin and grifolic acid by dioxinone-β-keto-acylation,
palladium catalyzed decarboxylative allylic rearrangement and aromatization
File(s)1-s2.0-S0040403917306925-TETL with Freeman.pdf (487.79 KB)
Accepted version
Author(s)
Ma, TK
White, AJP
Barrett, AGM
Type
Journal Article
Abstract
Biomimetic total syntheses of resorcinols amorphastilbol, grifolin and grifolic acid have been completed in four steps starting from geraniol and farnesol without the use of phenolic protection. The key steps involve C-acylation of dioxinone-β-keto esters, followed by palladium catalyzed decarboxylative allylic rearrangement and biomimetic aromatization.
Date Issued
2017-06-01
Date Acceptance
2017-05-31
Citation
Tetrahedron Letters, 2017, 58 (28), pp.2765-2767
ISSN
1873-3581
Publisher
Elseiver
Start Page
2765
End Page
2767
Journal / Book Title
Tetrahedron Letters
Volume
58
Issue
28
Copyright Statement
© 2017 Elsevier Ltd. All rights reserved. This manuscript is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International http://creativecommons.org/licenses/by-nc-nd/4.0/
Subjects
0305 Organic Chemistry
Publication Status
Published