110510-67-3Relevant academic research and scientific papers
Total Synthesis of (+/-)-Citreoviral, based on a Biogenetic Model, and Formal Synthesis of (+/-)-Citreoviridin
Bowden, Martin C.,Patel, Prakash,Pattenden, Gerald
, p. 1947 - 1950 (2007/10/02)
The total synthesis of (+/-)-citreoviral, which co-occurs with citreoviridin, citreoviridinol, and citreodiol in Penicillium citreoviride, is described.The synthesis is based on a biogenetic model, and has as a key feature the elaboration of the dihydroxytetrahydrofuranyl ring portion 10 by an acid-catalysed cyclisation of the central epoxy alcohol intermediate 9 which is derived in ten steps from methyl tiglate.
New Stereoselective Approach to Hydroxy-Substituted Tetrahydrofurans. Total Synthesis of (+/-)-Citreoviral
Begley, Michael J.,Bowden, Martin C.,Patel, Prakash,Pattenden, Gerald
, p. 1951 - 1958 (2007/10/02)
A concise total synthesis of (+/-)-citreoviral which illustrates a new stereoselective approach to hydroxy-substituted tetrahydrofurans is described.Key features in the synthesis are: (i) elaboration of the Z-unsaturated epoxy ester 10, (ii) acid-catalysed cyclisation of ester 10 to the 4-hydroxyethyl-substituted but-2-enolide 14, (iii) stereoselective vicinal hydroxylation of the butenolide 14 to the diol 15, (iv) cyclic ether formation from diol 15 to the bicyclic lactone 8 via the benzylidene acetal 9, (v) transesterification of bicycle 8 to the tetrahydrofuran 21 containing three of the four centres in citreoviral in the correct relative configuration.Inversion of the secondary 3-OH group in compound 21, and elaboration of the C-2 side-chain, then completed the synthesis of (+/-)-citreoviral.
Total Synthesis of (+/-)-Citreoviridin
Williams, D. R.,White, F. H.
, p. 5067 - 5079 (2007/10/02)
Investigations of iodine-induced cyclizations of γ,δ-olefinic benzyl ethers have led to highly substituted tetrahydrofurans from acyclic precursors with excellent stereochemical control.Our studies have afforded total syntheses of two fungal metabolites,
HYDROXYL-DIRECTED IODOETHERIFICATIONS OF ALLYLIC ALCOHOLS. SYNTHESIS OF ALLYLIC ALCOHOLS. SYNTHESSIS OF (+/-)-CITREOVIRAL.
Williams, D. R.,White, Franklin H.
, p. 2529 - 2532 (2007/10/02)
Iodine-induced cyclizations of γ,δ-olefinic benzyl ethers have afforded highly substituted tetrahydrofurans with complete stereocontrol as directed by the configuration of an allylic alcohol.Evidence for stereochemical assignments and conversion to citreo
