First consecutive linear synthesis of hostmaniene, 5-formyl-2- (isopropyl-l'-ol)benzofuran and anadendroic acid using prenylated phenol

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...

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Published in:Organic Communications
Main Author: Mohammat M.F.; Osman N.S.; Shaameri Z.; Hamzah A.S.
Format: Article
Language:English
Published: ACG Publications 2017
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
id 2-s2.0-85019671075
spelling 2-s2.0-85019671075
Mohammat M.F.; Osman N.S.; Shaameri Z.; Hamzah A.S.
First consecutive linear synthesis of hostmaniene, 5-formyl-2- (isopropyl-l'-ol)benzofuran and anadendroic acid using prenylated phenol
2017
Organic Communications
10
2
10.25135/acg.oc.17.17.03.011
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
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.
ACG Publications
13076175
English
Article
All Open Access; Gold Open Access
author Mohammat M.F.; Osman N.S.; Shaameri Z.; Hamzah A.S.
spellingShingle Mohammat M.F.; Osman N.S.; Shaameri Z.; Hamzah A.S.
First consecutive linear synthesis of hostmaniene, 5-formyl-2- (isopropyl-l'-ol)benzofuran and anadendroic acid using prenylated phenol
author_facet Mohammat M.F.; Osman N.S.; Shaameri Z.; Hamzah A.S.
author_sort Mohammat M.F.; Osman N.S.; Shaameri Z.; Hamzah A.S.
title First consecutive linear synthesis of hostmaniene, 5-formyl-2- (isopropyl-l'-ol)benzofuran and anadendroic acid using prenylated phenol
title_short First consecutive linear synthesis of hostmaniene, 5-formyl-2- (isopropyl-l'-ol)benzofuran and anadendroic acid using prenylated phenol
title_full First consecutive linear synthesis of hostmaniene, 5-formyl-2- (isopropyl-l'-ol)benzofuran and anadendroic acid using prenylated phenol
title_fullStr First consecutive linear synthesis of hostmaniene, 5-formyl-2- (isopropyl-l'-ol)benzofuran and anadendroic acid using prenylated phenol
title_full_unstemmed First consecutive linear synthesis of hostmaniene, 5-formyl-2- (isopropyl-l'-ol)benzofuran and anadendroic acid using prenylated phenol
title_sort First consecutive linear synthesis of hostmaniene, 5-formyl-2- (isopropyl-l'-ol)benzofuran and anadendroic acid using prenylated phenol
publishDate 2017
container_title Organic Communications
container_volume 10
container_issue 2
doi_str_mv 10.25135/acg.oc.17.17.03.011
url 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
description 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.
publisher ACG Publications
issn 13076175
language English
format Article
accesstype All Open Access; Gold Open Access
record_format scopus
collection Scopus
_version_ 1809677909142536192

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