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Diastereoselective radical cyclization reactions; the synthesis of O -methylcorytenchirine

Beckwith, Athelstan (Athel); Mayadunne, Roshan

Description

Highly diastereoselective cyclization of radicals such as 4 provides a model for the synthesis of 8-substituted berbines. Thus the reaction of 6,7-dimethoxyisoquinoline 21 with the acid chloride 19 affords the key intermediate 22, which undergoes free radical cyclization on treatment with tributylstannane to give (±)-23 as the sole product. Reduction of 23 affords (±)-O-methylcorytenchirine 14. The carbamate 24 does not undergo radical cyclization when treated with tributylstannane, but the...[Show more]

dc.contributor.authorBeckwith, Athelstan (Athel)
dc.contributor.authorMayadunne, Roshan
dc.date.accessioned2015-12-13T22:38:26Z
dc.date.available2015-12-13T22:38:26Z
dc.identifier.issn1551-7004
dc.identifier.urihttp://hdl.handle.net/1885/77553
dc.description.abstractHighly diastereoselective cyclization of radicals such as 4 provides a model for the synthesis of 8-substituted berbines. Thus the reaction of 6,7-dimethoxyisoquinoline 21 with the acid chloride 19 affords the key intermediate 22, which undergoes free radical cyclization on treatment with tributylstannane to give (±)-23 as the sole product. Reduction of 23 affords (±)-O-methylcorytenchirine 14. The carbamate 24 does not undergo radical cyclization when treated with tributylstannane, but the acetyl pyridine 33 affords the cyclized products 37 and 38 in reasonable yield and with good diastereoselectivity.
dc.publisherARKAT Foundation
dc.sourceARKIVOC
dc.source.urihttp://www.arkat-usa.org/ark/journal/2004/I10_Rickards/RI-1149C/RI-1149C.asp
dc.subjectKeywords: acid; berbine derivative; carbamic acid; chloride; isoquinoline; pyridine derivative; analytic method; article; cyclization; reaction analysis; stereochemistry; synthesis Alkaloids; Diastereoselectivity; O-methylcorytenchirine; Radical cyclization
dc.titleDiastereoselective radical cyclization reactions; the synthesis of O -methylcorytenchirine
dc.typeJournal article
local.description.notesImported from ARIES
local.description.refereedYes
local.identifier.citationvolume2004
dc.date.issued2004
local.identifier.absfor030503 - Organic Chemical Synthesis
local.identifier.ariespublicationMigratedxPub6396
local.type.statusPublished Version
local.contributor.affiliationBeckwith, Athelstan (Athel), College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationMayadunne, Roshan, College of Physical and Mathematical Sciences, ANU
local.bibliographicCitation.issuex
local.bibliographicCitation.startpage80
local.bibliographicCitation.lastpage93
dc.date.updated2015-12-11T09:43:48Z
local.identifier.scopusID2-s2.0-5044223643
CollectionsANU Research Publications

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