7-Demethylnaphterpin

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Category Others
Catalog number BBF-03720
CAS 137109-43-4
Molecular Weight 340.37
Molecular Formula C20H20O5

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Description

7-Demethylnaphterpin is a free radical scavenger produced by Streptomyces prunicololor.

Specification

Synonyms Naphthgeranine A

Properties

Appearance Yellow Powder
Boiling Point 553.7°C at 760 mmHg
Melting Point 217-218°C
Density 1.25 g/cm3

Reference Reading

1. Total Synthesis of Naphterpin and Marinone Natural Products
Lauren A M Murray, Thomas Fallon, Christopher J Sumby, Jonathan H George Org Lett. 2019 Oct 18;21(20):8312-8315. doi: 10.1021/acs.orglett.9b03095. Epub 2019 Sep 24.
A concise and divergent strategy for the synthesis of the naphterpin and marinone meroterpenoid families has been developed. The approach features a succession of pericyclic reactions-an aromatic Claisen rearrangement, a retro-6π-electrocyclization, and two Diels-Alder reactions-which facilitated the first total synthesis of naphterpin itself in five steps from 2,5-dimethoxyphenol, alongside similar syntheses of 7-demethylnaphterpin and debromomarinone. Late-stage oxidation and bromination reactions were also investigated, leading to the first total syntheses of naphterpins B and C and isomarinone.

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