97514-85-7

Upstream product

• 98095-59-1 (+/-)-(3R^*,4R^*)-4-(benzyloxy)-3-methyl-1-penten-3-ol 
• 110510-57-1 (+/-)-(2S^*,3S^*,4S^*,5R^*)-2-formyl-4-<(2-methoxyethoxy)methoxy>-2,4,5-trimethyl-3-tetrahydrofuranyl benzoate 
• 98168-76-4 (+/-)-(2S^*,3S^*,4R^*,5R^*)-4-<(2-methoxyethoxy)methoxy>-2,4,5-trimethyl-2-vinyl-3-tetrahydrofuranol 
• 98095-67-1 (+/-)-(2S^*,3R^*,4R^*,5R^*)-4-<(2-methoxyethoxy)methoxy>-2,4,5-trimethyl-2-vinyl-3-tetrahydrofuranol 
• 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 
• 98168-77-5 (+/-)-(2S^*,3S^*,4S^*,5R^*)-4-<(2-methoxyethoxy)methoxy>-2,4,5-trimethyl-2-vinyl-3-tetrahydrofuranyl benzoate 
• 107613-13-8 Benzoic acid (Z)-(R)-1-[(1R,2S)-2-benzyloxy-1-(2-methoxy-ethoxymethoxy)-1-methyl-propyl]-2-methyl-but-2-enyl ester 
• 102103-84-4 (2E,4E,6RS,7RS)-ethyl 6,7-isopropylidenedioxy-2,4,6-trimethylocta-2,4-dienoate 
• 497-02-9 (E)-2-methyl-2-buten-1-ol 
• 6622-76-0 methyl (E)-2-methyl-2-butenoate 
• 358750-37-5 (2S,3R)-2,3-Dimethyl-oxirane-2-carbaldehyde 
• 104417-93-8 (E)-ethyl 3(3α,4α-dihydroxy-2α,4β,5α-trimethyltetrahydrofuran-2β-yl)-2-methylpropenoate 
• 102103-86-6 (E)-3-[3-(1,2-Dihydroxy-1-methyl-propyl)-2-methyl-oxiranyl]-2-methyl-acrylic acid ethyl ester 

Relevant academic research and scientific papers

Synthesis of (+/-)-5-epi-citreoviral and (+/-)-citreoviral and the kinetic resolution of an allylic silane by a [3 + 2] annulation.

[reaction: see text] The [3 + 2] annulation reaction of allylsilane 1 with an alpha-keto ester provided the highly substituted tetrahydrofuran 2 as a single diastereomer in high yield. The synthesis of (+/-)-5-epi-citreoviral and (+/-)-citreoviral has bee

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.

Total Synthesis of (+/-)-Citreoviridin

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.

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