Total synthesis of the pseudopterosin aglycones.
@article{Newton2015TotalSO,
title={Total synthesis of the pseudopterosin aglycones.},
author={Christopher G. Newton and Michael S. Sherburn},
journal={Natural product reports},
year={2015},
volume={32 6},
pages={
865-76
}
}The pseudopterosin natural products have been the focus of a substantial number of synthetic studies since the first members were isolated almost 30 years ago. Herein we review all total and formal syntheses of this family of glycosylated diterpenes, with an emphasis on the synthetic strategies employed.
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References
SHOWING 1-10 OF 88 REFERENCES
Synthetic studies towards pseudopterosin A
- Chemistry
- 1996
The tricyclic hexahydrophenalene derivative (±)-8, a potential precursor for the synthesis of pseudopterosins, has been prepared in 5 steps from 4-methyl-cyclohex-2-enone 3.
A Synthesis of the Pseudopterosin A–F Aglycone
- Chemistry
- 2012
The synthesis of the pseudopterosin A–F aglycone from 3-methylcatechol features (a) the use of asymmetric Ireland–Claisen and aryl Claisen rearrangements to install three of the four stereocentres…
A synthetic approach to the pseudopterosins
- Chemistry
- 1996
Three Lewis acid catalysed reactions used in a synthesis of the tricyclic core of the marine anti-inflammatory pseudopterosins are reported; the reductive cleavage of an oxirane with inversion, the…
Synthetic approaches to pseudopterosin G aglycone dimethyl ether
- Chemistry
- 1998
Three successive reactions of a dimethoxy arene with allylic cation equivalents were used to convert 2,3-dimethoxy-4-methyl-1-iodobenzene to the hexahydro-1H-phenalene system of the potent marine…
Total Synthesis of Colombiasin A.
- ChemistryAngewandte Chemie
- 2001
Preliminary studies toward the asymmetric total synthesis of both enantiomers indicate that the determination of the absolute stereochemistry can be expected soon, and this structurally novel, biologically active tetracyclic compound has been synthesized for the first time in racemic form.
Enantiospecific total synthesis of pseudopterosins A and E
- Chemistry
- 1989
Preparation de ces composes a partir d'une oxime de cyclohexyl-2 propanal et d'un O-benzyl-2 fucose pour la pseudopterosine E ou d'une bromure de xylopyranosyle pour la pseudopterosine A



