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Asymmetric total synthesis of smyrindiol employing an organocatalytic aldol key step.

ABSTRACT: 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.

SUBMITTER: Enders D

PROVIDER: S-EPMC3458728 | biostudies-other | 2012

REPOSITORIES: biostudies-other

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Asymmetric total synthesis of smyrindiol employing an organocatalytic aldol key step.

Enders Dieter D Fronert Jeanne J Bisschops Tom T Boeck Florian F

Beilstein journal of organic chemistry 20120718

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. ...[more]

PMID: 23019438

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