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The total synthesis of (-)-connatusin A, a hirsutane-type sesquiterpene isolated from the fungus Lentinus connatus BCC8996

Bon, David J.-Y. D; Banwell, Martin; Cade, Ian; Willis, Anthony

Description

The title sesquiterpenoid natural product 1 has been prepared for the first time using the enantiomerically pure cis-1,2-dihydrocatechol 3 as starting material. Key steps associated with the synthesis include a Diels-Alder cycloaddition reaction of the acetonide 5 with cyclopentenone (4) and an oxa-di-π-methane rearrangement of bicylco[2.2.2]octenone 6 derived from the initial adduct. The product of this sequence, the cyclopropannulated triquinane 7, was elaborated, over a further eight steps...[Show more]

dc.contributor.authorBon, David J.-Y. D
dc.contributor.authorBanwell, Martin
dc.contributor.authorCade, Ian
dc.contributor.authorWillis, Anthony
dc.date.accessioned2015-12-10T22:55:28Z
dc.identifier.issn0040-4020
dc.identifier.urihttp://hdl.handle.net/1885/60133
dc.description.abstractThe title sesquiterpenoid natural product 1 has been prepared for the first time using the enantiomerically pure cis-1,2-dihydrocatechol 3 as starting material. Key steps associated with the synthesis include a Diels-Alder cycloaddition reaction of the acetonide 5 with cyclopentenone (4) and an oxa-di-π-methane rearrangement of bicylco[2.2.2]octenone 6 derived from the initial adduct. The product of this sequence, the cyclopropannulated triquinane 7, was elaborated, over a further eight steps including those involving Upjohn dihydroxylation and Swern oxidation protocols, to the target 1. A single-crystal X-ray analysis served to confirm the structure of this synthetically derived material.
dc.publisherElsevier
dc.sourceTetrahedron
dc.subjectKeywords: catechol; connatusin a; cyclopentenone; methane; sesquiterpene; unclassified drug; 1,2 dihydrocatechol; article; cycloaddition; Diels Alder reaction; drug isolation; drug structure; drug synthesis; enantiomer; hydroxylation; Lentinus; Lentinus connatus; p Chemoenzymatic; Connatusin A; Diels-Alder; Oxa-di-p-methane; Photochemistry; Sesquiterpene
dc.titleThe total synthesis of (-)-connatusin A, a hirsutane-type sesquiterpene isolated from the fungus Lentinus connatus BCC8996
dc.typeJournal article
local.description.notesImported from ARIES
local.identifier.citationvolume67
dc.date.issued2011
local.identifier.absfor030502 - Natural Products Chemistry
local.identifier.ariespublicationu4005981xPUB524
local.type.statusPublished Version
local.contributor.affiliationBon, David J.-Y. D, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationBanwell, Martin, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationCade, Ian, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationWillis, Anthony, College of Physical and Mathematical Sciences, ANU
local.description.embargo2037-12-31
local.bibliographicCitation.issue43
local.bibliographicCitation.startpage8348
local.bibliographicCitation.lastpage8352
local.identifier.doi10.1016/j.tet.2011.08.057
local.identifier.absseo970103 - Expanding Knowledge in the Chemical Sciences
dc.date.updated2016-02-24T10:24:32Z
local.identifier.scopusID2-s2.0-80053054288
local.identifier.thomsonID000295662600018
CollectionsANU Research Publications

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