Synthesis of Spiroketals Related to Griseusin A

Show simple item record Brimble, MA en Nairn, MR en 2011-09-21T22:02:42Z en 1996 en
dc.identifier.citation Molecules 1(1):3-14 1996 en
dc.identifier.issn 1431-5157 en
dc.identifier.uri en
dc.description.abstract The synthesis and attempted functionalization of the spiroketal ring system of the naturally occurring pyranonaphthoquinone antibiotic griseusin A 1 is reported. The unsaturated spiroketals 5,6 were prepared from furonaphthopyran 22, which in turn was constructed from furonaphthofuran 20. Addition of 2-trimethylsilyloxyfuran 13 to quinone 19 afforded furonaphthofuran 20. Initial work using acetylenic quinone 12 afforded a pentacyclic product 15, where a third Michael reaction of the phenolic hydroxyl group with the α,β-unsaturated ketone moiety had occurred. Modified reaction conditions afforded trimethylsilyl analogue 16. Naphthoquinone 19, which bears a 2-alkenyl side chain rather than an acetylene, was synthesized using similar methodology to 12 and subsequently converted to furonaphthofuran adduct 20. Ceric ammonium nitrate oxidative rearrangement of 20 produced diol 22, which was then cyclized to spiroketals 5,6 under acidic conditions. Reaction of spiroacetals 5,6 with osmium tetroxide did not effect the desired hydroxylation of the olefin. Use of cetyltrimethylammonium permanganate as the hydroxylation reagent resulted in reaction with the C5a-C11a double bond affording diols 24,25. en
dc.relation.ispartofseries Molecules en
dc.rights Items in ResearchSpace are protected by copyright, with all rights reserved, unless otherwise indicated. Previously published items are made available in accordance with the copyright policy of the publisher. Details obtained from en
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dc.title Synthesis of Spiroketals Related to Griseusin A en
dc.type Journal Article en
dc.identifier.doi 10.1007/s007830050002 en
pubs.begin-page 3 en
pubs.volume 13 en
dc.rights.holder Copyright: 1996 Springer-Verlag en
pubs.end-page 14 en
dc.rights.accessrights en
pubs.subtype Article en
pubs.elements-id 39884 en Science en Chemistry en Science Research en Maurice Wilkins Centre (2010-2014) en
pubs.record-created-at-source-date 2010-09-01 en

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