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- W2007481010 abstract "A chemo-enzymatic approach to (R,R)-(-)-pyrenophorin starting from commercially available 6-methyl-5-hepten-2-one is described. Firstly, (R)-6-methyl-5-hepten-2-ol (sulcatol) was prepared by interface-bioreactor mediated asymmetric reduction of the corresponding ketone by a yeast, Pichia farinosa IAM 4682 (51% yield, 90%e.e.). The sequential carbon-chain elongation via Horner-Emmons olefination of protected aldehyde and cyanation afforded all of carbon skeleton in the seco acid with a desired β,γ-(E)-double bond. By the aid of a microorganism, Rhodococcus rhodochrous IFO15564, the nitrile was efficiently hydrolyzed to give the corresponding carboxylic acid, (R,E)-7-hydroxy-3-octenoate, the key synthetic intermediate without affecting the position and configuration of the double bond (90% yield). Dimeric lactone structure was obtained by utilizing a lipase-catalyzed lactonization. While Pseudomonas cepacia lipase-catalyzed reaction worked in a moderate efficiency, higher yield of desired dimeric lactone (44%) was obtained by the use of an immobilized form of Candida antarctica lipase. The lactonization was accelerated in the presence of molecular sieves 4A. (R,R)-(-)-Pyrenophorin was obtained from this dimeric lactone (Seebach's intermediate) by the subsequent chemical transformation." @default.
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- W2007481010 date "1995-10-01" @default.
- W2007481010 modified "2023-09-23" @default.
- W2007481010 title "Chemo-enzymatic synthesis of (R,R)-(-)-Pyrenophorin" @default.
- W2007481010 cites W1480271304 @default.
- W2007481010 cites W1967213454 @default.
- W2007481010 cites W1969236345 @default.
- W2007481010 cites W1970695365 @default.
- W2007481010 cites W1971743609 @default.
- W2007481010 cites W1975625140 @default.
- W2007481010 cites W1977902174 @default.
- W2007481010 cites W1982892157 @default.
- W2007481010 cites W1983634695 @default.
- W2007481010 cites W1984488325 @default.
- W2007481010 cites W1986549517 @default.
- W2007481010 cites W1988152917 @default.
- W2007481010 cites W1988328518 @default.
- W2007481010 cites W1992040136 @default.
- W2007481010 cites W1992723030 @default.
- W2007481010 cites W1993610536 @default.
- W2007481010 cites W1996054932 @default.
- W2007481010 cites W2000232561 @default.
- W2007481010 cites W2003644865 @default.
- W2007481010 cites W2004407126 @default.
- W2007481010 cites W2005767400 @default.
- W2007481010 cites W2011491082 @default.
- W2007481010 cites W2012573588 @default.
- W2007481010 cites W2015320259 @default.
- W2007481010 cites W2016162852 @default.
- W2007481010 cites W2016473365 @default.
- W2007481010 cites W2019929907 @default.
- W2007481010 cites W2023949116 @default.
- W2007481010 cites W2030037441 @default.
- W2007481010 cites W2031799240 @default.
- W2007481010 cites W2031904477 @default.
- W2007481010 cites W2033751845 @default.
- W2007481010 cites W2035982911 @default.
- W2007481010 cites W2036731267 @default.
- W2007481010 cites W2036755883 @default.
- W2007481010 cites W2042896521 @default.
- W2007481010 cites W2045030535 @default.
- W2007481010 cites W2048741637 @default.
- W2007481010 cites W2053125842 @default.
- W2007481010 cites W2053999988 @default.
- W2007481010 cites W2054527626 @default.
- W2007481010 cites W2060559112 @default.
- W2007481010 cites W2063633338 @default.
- W2007481010 cites W2064698603 @default.
- W2007481010 cites W2067270459 @default.
- W2007481010 cites W2071475175 @default.
- W2007481010 cites W2074480514 @default.
- W2007481010 cites W2079212750 @default.
- W2007481010 cites W2080547412 @default.
- W2007481010 cites W2084751397 @default.
- W2007481010 cites W2085047228 @default.
- W2007481010 cites W2087745669 @default.
- W2007481010 cites W2089598658 @default.
- W2007481010 cites W2090005970 @default.
- W2007481010 cites W2092465074 @default.
- W2007481010 cites W2095004489 @default.
- W2007481010 cites W2095453715 @default.
- W2007481010 cites W2111310989 @default.
- W2007481010 cites W2116325139 @default.
- W2007481010 cites W2125745394 @default.
- W2007481010 cites W2131181454 @default.
- W2007481010 cites W2131817747 @default.
- W2007481010 cites W2138956181 @default.
- W2007481010 cites W2150454507 @default.
- W2007481010 cites W2156245902 @default.
- W2007481010 cites W2162591534 @default.
- W2007481010 cites W2162957773 @default.
- W2007481010 cites W2164103514 @default.
- W2007481010 cites W2342408329 @default.
- W2007481010 cites W2950131500 @default.
- W2007481010 cites W2950528301 @default.
- W2007481010 cites W2950535336 @default.
- W2007481010 cites W2950754207 @default.
- W2007481010 cites W2950914910 @default.
- W2007481010 cites W2951044346 @default.
- W2007481010 cites W2951076182 @default.
- W2007481010 cites W2951882408 @default.
- W2007481010 cites W2952394062 @default.
- W2007481010 cites W2952399000 @default.
- W2007481010 cites W2953257783 @default.
- W2007481010 cites W2953269193 @default.
- W2007481010 cites W3005264824 @default.
- W2007481010 cites W4239229489 @default.
- W2007481010 cites W4253617805 @default.
- W2007481010 doi "https://doi.org/10.1016/0040-4020(95)00758-z" @default.
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