102104-01-8Relevant academic research and scientific papers
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 (+)-CITREOVIRAL
Bowden, Martin C.,Pattenden, Gerald
, p. 711 - 714 (2007/10/02)
A total synthesis of (+)-citreoviral (1) found in Penicillium citreoviride, which uses the bicyclic lactone (5) as a key intermediate, is described.
