96745-47-0

Upstream product

• 110510-55-9 (2S,4R,5S)-2-((S)-1-Iodo-ethyl)-4-(2-methoxy-ethoxymethoxy)-2,4,5-trimethyl-dihydro-furan-3-one 
• 98095-68-2 (+/-)-(2S^*,4S^*,5R^*)-4-<(2-methoxyethoxy)methoxy>-2,4,5-trimethyl-2-vinyl-3-tetrahydrofuranone 
• 104417-93-8 (E)-ethyl 3-(3β,4α-dihydroxy-2β,4β,5α-trimethyltetrahydrofuran-2α-yl)-2-methylpropenoate 
• 96701-23-4 (E)-3-((2R,3S,4R,5R)-3,4-Dihydroxy-2,4,5-trimethyl-tetrahydro-furan-2-yl)-2-methyl-acrylic acid methyl ester 
• 497-02-9 (E)-2-methyl-2-buten-1-ol 
• 102103-91-3 (2Z,4RS,5RS)-methyl epoxy-2,4-dimethylhex-2-enoate 
• 102103-95-7 methyl 3α,4α-dihydroxy-2β,4β,5β-trimethyltetrahydrofuran-2α-carboxylate 
• 102103-97-9 3α,4α-isopropylidenedioxy-2β,4β,5β-trimethyltetrahydrofuran-2α-carbaldehyde 
• 104417-93-8 (E)-ethyl 3-(3α,4α-dihydroxy-2β,4β,5β-trimethyltetrahydrofuran-2α-yl)-2-methylpropenoate 
• 102103-98-0 (E)-ethyl 3-(3α,4α-isopropylidenedioxy-2β,4β,5β-trimethyltetrahydrofuran-2α-yl)-2-methylpropenoate 
• 6622-76-0 methyl (E)-2-methyl-2-butenoate 
• 102103-89-9 (E)-3(3α,4α-dihydroxy-2α,4β,5α-trimethyltetrahydrofuran-2β-yl)-2-methylpropen-1-ol 
• 102103-83-3 (2E,4RS,5RS)-4,5-isopropylidenedioxy-2,4-dimethylhex-2-enal 
• 102103-85-5 (2E,4E,6RS,7RS)-ethyl 6,7-dihydroxy-2,4,6-trimethylocta-2,4-dienoate 

Relevant academic research and scientific papers

Total Synthesis of (+/-)-Citreoviral, based on a Biogenetic Model, and Formal Synthesis of (+/-)-Citreoviridin

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

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.

HYDROXYL-DIRECTED IODOETHERIFICATIONS OF ALLYLIC ALCOHOLS. SYNTHESIS OF ALLYLIC ALCOHOLS. SYNTHESSIS OF (+/-)-CITREOVIRAL.

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