94120-02-2Relevant academic research and scientific papers
Highly efficient total synthesis of (+)-citreoviral
Murata, Yoshihisa,Kamino, Tomoyuki,Aoki, Toshiaki,Hosokawa, Seijiro,Kobayashi, Susumu
, p. 3175 - 3177 (2007/10/03)
Only eight steps were required for the total synthesis of (+)-citreoviral (3) from chiral imide 1 in 18% overall yield. The key steps included a highly anti-selective aldol reaction, the stereoselective iodolactonization of a γ,δ-unsaturated β-hydroxyimid
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 (+)-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.
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
ENANTIOSELECTIVE SYNTHESIS OF (+)-CITREOVIRAL USING ASYMMETRIC HYDROXYLATION OF TIGLATE ESTERS
Hatakeyama, Susumi,Matsui, Yumiko,Suzuki, Masahiro,Sakurai, Kuniya,Takano, Seiichi
, p. 6485 - 6488 (2007/10/02)
A microbial metabolite (+)-citreoviral has been synthesized enantio- and stereo-selectively using newly developed asymmetric hydroxylation of tiglate esters for the construction of the key chiral building block.
Isolation and stereostructures of citreoviral, citreodiol, and epicitreodiol
Shizuri,Nishiyama,Imai,Yamamura
, p. 4771 - 4774 (2007/10/02)
Three new metabolites (citreoviral, citreodiol, and epicitreodiol) have been isolated from the mycelium of Penicillium citreo-viride B. (IFO 6050) and their stereostructures have been elucidated on the basis of their spectral data coupled with some chemical evidence. Furthermore, the absolute configurations of citreodiol and epicitreodiol have been determined by synthesis of the corresponding antipodes starting from L-rhamnose.
