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Asymmetric Total Synthesis of (+)-O-methylasparvenone, a Rare Nitrogen-Free Serotonin 2C Receptor Antagonist

Asymmetric Total Synthesis of (+)-O-methylasparvenone, a Rare Nitrogen-Free Serotonin 2C Receptor Antagonist

Raphaël Lafleur-Lambert, John Boukouvalas

Org Biomol Chem. 2016 Sep 21;14(37):8758-8763.

PMID: 27714191

Abstract:

The first enantioselective synthesis of the fungal metabolite (+)-O-methylasparvenone was achieved in eight steps and 22% overall yield from inexpensive 3,4,5-trimethoxybenzaldehyde dimethyl acetal. Key steps include (i) early-stage asymmetric alkynylation of an aromatic aldehyde with a propiolate, (ii) intramolecular Friedel-Crafts acylation, and (iii) site-selective cleavage of an aryl methyl ether.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP1125888	Benzaldehyde dimethyl acetal		1125-88-8	Price

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