First consecutive linear synthesis of hostmaniene, 5-formyl-2- (isopropyl-l'-ol)benzofuran and anadendroic acid using prenylated phenol
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]cycl...
| Published in: | Organic Communications |
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| Main Author: | |
| Format: | Article |
| Language: | English |
| Published: |
ACG Publications
2017
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| Online Access: | https://www.scopus.com/inward/record.uri?eid=2-s2.0-85019671075&doi=10.25135%2facg.oc.17.17.03.011&partnerID=40&md5=9770ed08253d729ea7b4e166260b2c53 |
| Summary: | 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. © 2017 ACG Publications. |
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| ISSN: | 13076175 |
| DOI: | 10.25135/acg.oc.17.17.03.011 |