Asymmetric total synthesis of smyrindiol employing an organocatalytic aldol key step

Asymmetric total synthesis of smyrindiol employing an organocatalytic aldol key step

The first organocatalytic asymmetric synthesis of smyrindiol, by using an (S)-proline catalyzed enantioselective intramolecular aldol reaction as the key step, is described. Smyrindiol was synthesized from commercially available 2,4-dihydroxybenzaldehyde in 15 steps, with excellent stereoselectivity...

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Bibliographic Details
Main Authors: Dieter Enders, Jeanne Fronert, Tom Bisschops, Florian Boeck
Format: Article
Language:English
Published: Beilstein-Institut 2012-07-01
Series:Beilstein Journal of Organic Chemistry
Subjects:
aldol reaction
asymmetric synthesis
organocatalysis
proline
smyrindiol
Online Access:https://doi.org/10.3762/bjoc.8.123
Description
Summary:The first organocatalytic asymmetric synthesis of smyrindiol, by using an (S)-proline catalyzed enantioselective intramolecular aldol reaction as the key step, is described. Smyrindiol was synthesized from commercially available 2,4-dihydroxybenzaldehyde in 15 steps, with excellent stereoselectivity (de = 99%, ee = 99%). In the course of this total synthesis a new and mild coumarin assembly was developed.
ISSN:1860-5397

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