Matches in SemOpenAlex for { <https://semopenalex.org/work/W3138457910> ?p ?o ?g. }
- W3138457910 endingPage "1996" @default.
- W3138457910 startingPage "1983" @default.
- W3138457910 abstract "Main observation and conclusion A full account of the total synthesis of (–)‐pallambins A—D (1—6) is described. The strategy was devised by simulating their biosynthetic pathway. The left‐part bicyclo[3.2.1]octane system of pallambins C and D was efficiently constructed via a palladium‐ catalyzed oxidative cyclization. For construction of the right‐part tetrahydrofuran/γ‐lactone moiety (C/D rings), initial attempts to synthesize the allylic alcohol 15 for an one‐step Pd‐mediated alkoxycarbonylation have failed. However, during the course of this work, an unprecedented CH 3 Li‐mediated method for conversion of bromoisoxazoline to the corresponding β‐hydroxy nitrile has been discovered. Furthermore, a stepwise protocol was designed, namely an Eschenmoser‐Claisen rearrangement/Lactonization to generate the C ring, and a non‐classical Wittig reaction to form the D ring. During the course of this work, a palladium‐catalyzed method for dehydrobromination of bromide ketone was developed. Finally, an individual transformation of pallambins C (3) and D (4) generated pallambins A (5) and B (6) under mild UV irradiation. Thus, the first enantioselective total syntheses of (–)‐pallambins A—D have been achieved in 15 or 16 steps from the known chiral cyclohexenone 8. The described synthesis avoids protecting‐group manipulations by designing highly chemo‐ and stereoselective transformations." @default.
- W3138457910 created "2021-03-29" @default.
- W3138457910 creator A5013587375 @default.
- W3138457910 creator A5014145981 @default.
- W3138457910 creator A5017774638 @default.
- W3138457910 creator A5023022769 @default.
- W3138457910 creator A5053726609 @default.
- W3138457910 date "2021-06-04" @default.
- W3138457910 modified "2023-10-18" @default.
- W3138457910 title "<scp>Protecting‐Group‐Free</scp> Total Synthesis of (–)‐Pallambins A—D" @default.
- W3138457910 cites W1563131412 @default.
- W3138457910 cites W1897111838 @default.
- W3138457910 cites W1916349588 @default.
- W3138457910 cites W1926190860 @default.
- W3138457910 cites W1967679714 @default.
- W3138457910 cites W1972171421 @default.
- W3138457910 cites W1973675119 @default.
- W3138457910 cites W1974930488 @default.
- W3138457910 cites W1980162026 @default.
- W3138457910 cites W1983333264 @default.
- W3138457910 cites W1985958610 @default.
- W3138457910 cites W1988428136 @default.
- W3138457910 cites W1989587348 @default.
- W3138457910 cites W1991819820 @default.
- W3138457910 cites W2000603712 @default.
- W3138457910 cites W2002263304 @default.
- W3138457910 cites W2003671960 @default.
- W3138457910 cites W2011618872 @default.
- W3138457910 cites W2012491239 @default.
- W3138457910 cites W2013348657 @default.
- W3138457910 cites W2026772670 @default.
- W3138457910 cites W2037355077 @default.
- W3138457910 cites W2042046522 @default.
- W3138457910 cites W2046013229 @default.
- W3138457910 cites W2051613947 @default.
- W3138457910 cites W2055280895 @default.
- W3138457910 cites W2060028507 @default.
- W3138457910 cites W2063576832 @default.
- W3138457910 cites W2069194725 @default.
- W3138457910 cites W2075384695 @default.
- W3138457910 cites W2078141729 @default.
- W3138457910 cites W2079152683 @default.
- W3138457910 cites W2082795593 @default.
- W3138457910 cites W2087639482 @default.
- W3138457910 cites W2090425997 @default.
- W3138457910 cites W2091636237 @default.
- W3138457910 cites W2097255795 @default.
- W3138457910 cites W2104118061 @default.
- W3138457910 cites W2105191573 @default.
- W3138457910 cites W2107977759 @default.
- W3138457910 cites W2108582504 @default.
- W3138457910 cites W2112297984 @default.
- W3138457910 cites W2115676169 @default.
- W3138457910 cites W2141471123 @default.
- W3138457910 cites W2161191498 @default.
- W3138457910 cites W2180404343 @default.
- W3138457910 cites W2236616254 @default.
- W3138457910 cites W2280460668 @default.
- W3138457910 cites W2314390500 @default.
- W3138457910 cites W2320339651 @default.
- W3138457910 cites W2324148780 @default.
- W3138457910 cites W2328141681 @default.
- W3138457910 cites W2334603899 @default.
- W3138457910 cites W2334919728 @default.
- W3138457910 cites W2414148776 @default.
- W3138457910 cites W2532754875 @default.
- W3138457910 cites W2549398017 @default.
- W3138457910 cites W2606270925 @default.
- W3138457910 cites W2606516237 @default.
- W3138457910 cites W2620626984 @default.
- W3138457910 cites W2751707274 @default.
- W3138457910 cites W2782672337 @default.
- W3138457910 cites W2803544643 @default.
- W3138457910 cites W2913374611 @default.
- W3138457910 cites W2920746881 @default.
- W3138457910 cites W2921269993 @default.
- W3138457910 cites W2949144543 @default.
- W3138457910 cites W2949697041 @default.
- W3138457910 cites W2950042821 @default.
- W3138457910 cites W2950299590 @default.
- W3138457910 cites W2950397158 @default.
- W3138457910 cites W2950441121 @default.
- W3138457910 cites W2951090638 @default.
- W3138457910 cites W2951393214 @default.
- W3138457910 cites W2951719189 @default.
- W3138457910 cites W2952001785 @default.
- W3138457910 cites W2952235419 @default.
- W3138457910 cites W2952604160 @default.
- W3138457910 cites W2962603266 @default.
- W3138457910 cites W3005420656 @default.
- W3138457910 cites W4250005087 @default.
- W3138457910 cites W4293916755 @default.
- W3138457910 cites W4377077259 @default.
- W3138457910 cites W2039384103 @default.
- W3138457910 doi "https://doi.org/10.1002/cjoc.202100001" @default.
- W3138457910 hasPublicationYear "2021" @default.
- W3138457910 type Work @default.
- W3138457910 sameAs 3138457910 @default.