Matches in SemOpenAlex for { <https://semopenalex.org/work/W2133731930> ?p ?o ?g. }
- W2133731930 endingPage "5212" @default.
- W2133731930 startingPage "5212" @default.
- W2133731930 abstract "epi-Jasmonic acid (epi-JA) and tuberonic acid (TA) were synthesized from the key aldehyde, all cis-2-(2-hydroxy-5-vinylcyclopentyl)acetaldehyde (14), which was in turn prepared stereoselectively from the (1R)-acetate of 4-cyclopentene-1,3-diol (10) through SN2-type allylic substitution with CH2CHMgBr followed by Mitsunobu inversion, Eschenmoser–Claisen rearrangement, and regioselective Swern oxidation of the corresponding bis-TES ether (13). Wittig reaction of the aldehyde 14 with [Ph3P(CH2)Me]+Br− followed by oxidation afforded epi-JA (3) stereoselectivity over the trans isomer. Similarly, TA (5) was synthesized. Furthermore, the above findings were applied successfully to improve the total efficiency of the previous synthesis of 12-oxo-PDA (1)." @default.
- W2133731930 created "2016-06-24" @default.
- W2133731930 creator A5012912592 @default.
- W2133731930 creator A5032131372 @default.
- W2133731930 creator A5048606699 @default.
- W2133731930 creator A5056073174 @default.
- W2133731930 creator A5090785823 @default.
- W2133731930 date "2010-01-01" @default.
- W2133731930 modified "2023-09-23" @default.
- W2133731930 title "Stereoselective synthesis of epi-jasmonic acid, tuberonic acid, and 12-oxo-PDA" @default.
- W2133731930 cites W1529372271 @default.
- W2133731930 cites W1759713136 @default.
- W2133731930 cites W1963905716 @default.
- W2133731930 cites W1969134270 @default.
- W2133731930 cites W1971983816 @default.
- W2133731930 cites W1974861963 @default.
- W2133731930 cites W1975185153 @default.
- W2133731930 cites W1978448175 @default.
- W2133731930 cites W1978702729 @default.
- W2133731930 cites W1978733875 @default.
- W2133731930 cites W1986292144 @default.
- W2133731930 cites W1986831149 @default.
- W2133731930 cites W1987874047 @default.
- W2133731930 cites W1992545780 @default.
- W2133731930 cites W1995043149 @default.
- W2133731930 cites W1995916411 @default.
- W2133731930 cites W1997106690 @default.
- W2133731930 cites W1997475185 @default.
- W2133731930 cites W1998627854 @default.
- W2133731930 cites W1999475521 @default.
- W2133731930 cites W2001424402 @default.
- W2133731930 cites W2001897814 @default.
- W2133731930 cites W2003215139 @default.
- W2133731930 cites W2003334563 @default.
- W2133731930 cites W2003404062 @default.
- W2133731930 cites W2003899630 @default.
- W2133731930 cites W2005778317 @default.
- W2133731930 cites W2009893156 @default.
- W2133731930 cites W2012477189 @default.
- W2133731930 cites W2017885675 @default.
- W2133731930 cites W2018113598 @default.
- W2133731930 cites W2018626341 @default.
- W2133731930 cites W2020036746 @default.
- W2133731930 cites W2021010520 @default.
- W2133731930 cites W2024157614 @default.
- W2133731930 cites W2025975183 @default.
- W2133731930 cites W2027291779 @default.
- W2133731930 cites W2027468888 @default.
- W2133731930 cites W2031196135 @default.
- W2133731930 cites W2036165278 @default.
- W2133731930 cites W2038256123 @default.
- W2133731930 cites W2038317963 @default.
- W2133731930 cites W2040532454 @default.
- W2133731930 cites W2042957856 @default.
- W2133731930 cites W2043676058 @default.
- W2133731930 cites W2044301975 @default.
- W2133731930 cites W2047215391 @default.
- W2133731930 cites W2052474233 @default.
- W2133731930 cites W2053011820 @default.
- W2133731930 cites W2056294130 @default.
- W2133731930 cites W2057954947 @default.
- W2133731930 cites W2059302633 @default.
- W2133731930 cites W2062343060 @default.
- W2133731930 cites W2062594764 @default.
- W2133731930 cites W2064691692 @default.
- W2133731930 cites W2066558828 @default.
- W2133731930 cites W2068825068 @default.
- W2133731930 cites W2073157289 @default.
- W2133731930 cites W2074425205 @default.
- W2133731930 cites W2075225814 @default.
- W2133731930 cites W2077160890 @default.
- W2133731930 cites W2079919041 @default.
- W2133731930 cites W2081050527 @default.
- W2133731930 cites W2084720613 @default.
- W2133731930 cites W2091206029 @default.
- W2133731930 cites W2092787925 @default.
- W2133731930 cites W2095202132 @default.
- W2133731930 cites W2095382928 @default.
- W2133731930 cites W2097634597 @default.
- W2133731930 cites W2099605015 @default.
- W2133731930 cites W2102758947 @default.
- W2133731930 cites W2114973337 @default.
- W2133731930 cites W2128233602 @default.
- W2133731930 cites W2129938408 @default.
- W2133731930 cites W2131083560 @default.
- W2133731930 cites W2153403643 @default.
- W2133731930 cites W2160863107 @default.
- W2133731930 cites W2161411468 @default.
- W2133731930 cites W2161760565 @default.
- W2133731930 cites W2177682486 @default.
- W2133731930 cites W233628489 @default.
- W2133731930 cites W2397256488 @default.
- W2133731930 cites W2813333070 @default.
- W2133731930 cites W2949565736 @default.
- W2133731930 cites W2949729870 @default.
- W2133731930 cites W2950741464 @default.
- W2133731930 cites W2951589706 @default.
- W2133731930 cites W2952548282 @default.