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- Title
First consecutive linear synthesis of hostmaniene, 5-formyl-2-(isopropyl-1'-ol)benzofuran and anadendroic acid using prenylated phenol.
- Authors
Mohammat, Mohd Fazli; Osman, Nur Shazwani; Shaameri, Zurina; Hamzah, Ahmad Sazali
- Abstract
The paper describes a new pathway for the syntheses of three natural bioactive benzofuran type compounds, namely, hostmaniene, 5-formyl-2-(isopropyl-1'-ol)benzofuran and anadendroic acid. The key synthetic strategy involved prenylation of the carboxy-phenol 7 and followed by the [5-exo-tet]cyclization reaction to furnish the benzofuran ring synthon. Subsequently, performing sequences of reactions of epoxide ring opening, ester reduction and re-oxidation of the alcohol from the benzofuran ring synthon gave all the title compounds in reasonable yield. Their structures were confirmed by both spectroscopic data and chemical transformations.
- Subjects
BENZOFURAN synthesis; BIOACTIVE compounds; RING formation (Chemistry); EPOXY compounds; RING-opening reactions; PHENOL
- Publication
Organic Communications, 2017, Vol 10, Issue 2, p130
- ISSN
1307-6175
- Publication type
Article
- DOI
10.25135/acg.oc.17.17.03.011