72523-81-0Relevant articles and documents
Total Synthesis of Preaurovertin, Putative Biogenetic Precursor of Aurovertin. Biosynthetic Interrelationships between the Aurovertins, Citreoviridinols and Asteltoxin
Forbes, Judith E.,Pattenden, Gerald
, p. 1959 - 1966 (2007/10/02)
A number of complementary biomimetic approaches to the tetrahydrofuranyl portion of the dienal 13, which was used in a synthesis of preaurovertin, are described.Epoxidation of the trienoate 31 produces largely the β-epoxide 32, which on treatment with aqueous trifluoroacetic acid undergoes deacetalisation and concomitant cyclisation leading to compound 34.After conversion of 34 into dienal 13, a Wittig reaction with the ylide derived from the phosphonium salt 37 produces preaurovertin.Preaurovertin is a putative biogenetic precursor of aurovertin found in Calcarisporium arbuscula.Citreoviridin produced by Penicillium citreoviride relates to preaurovertin, and the citreoviridinols are related structurally to aurovertin.In addition, aurovertin is related biogenetically to asteltoxin found in Aspergillus stellatus.These structural and biosynthetic interrelationships are considered alongside the synthetic work.
EPOXIDES IN SYNTHESIS. STUDIES TOWARDS THE AUROVERTINS
Forbes, Judith E.,Pattenden, Gerald
, p. 2771 - 2774 (2007/10/02)
A synthesis of the 2,6-dioxabicyclooctane ring system (16) found in the natural aurovertins e. g. (1), based on a biogenetic model (Scheme 1) and using two key epoxide cyclisation steps viz (12) (13) and (14) (16a), is described.
Enantioselective Syntheses using Chiral Epoxy-alcohols
Colvin, Ernest W.,Robertson, Alan D.,Wakharkar, Shaila
, p. 312 - 314 (2007/10/02)
The epoxy-alcohol (1, R=CH2Ph) opens under acid catalysis by attack at the proximate carbon atom.
Acyclic Stereoselection. 9. Stereochemistry of the Addition of Lithium Enolates to α-Alkoxy Aldehydes
Heathcock, Clayton H.,Young, Steven D.,Hagen, James P.,Pirrung, Michael C.,White, Charles T.,VanDerveer, Don
, p. 3846 - 3856 (2007/10/02)
The stereochemistry of addition of lithium enolates derived from esters and ketones to the α-alkoxy aldehydes 1-5 has been investigated.In all cases, the predominant product is that predicted by application of Felkin's model for asymmetric induction and by assuming the alkoxy group to be the "large" group.The Cram cyclic model for asymmetric induction is not followed.Stereostructures have been assigned by a combination of conversion to products of known stereostructure, 13C and 1H NMR correlations, and single-crystal X-ray analysis.
