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- W2800247243 abstract "(+)-Psiguadial B is a diformyl phloroglucinol meroterpenoid that exhibits antiproliferative activity against the HepG2 human hepatoma cancer cell line. This full account details the evolution of a strategy that culminated in the first enantioselective total synthesis of (+)-psiguadial B. A key feature of the synthesis is the construction of the trans-cyclobutane motif by a Wolff rearrangement with in situ catalytic, asymmetric trapping of the ketene. An investigation of the substrate scope of this method to prepare enantioenriched 8-aminoquinolinamides is disclosed. Three routes toward (+)-psiguadial B were evaluated that featured the following key steps: (1) an ortho-quinone methide hetero-Diels–Alder cycloaddition to prepare the chroman framework, (2) a Prins cyclization to form the bridging bicyclo[4.3.1]decane system, and (3) a modified Norrish–Yang cyclization to generate the chroman. Ultimately, the successful strategy employed a ring-closing metathesis to form the seven-membered ring and an intramolecular O-arylation reaction to complete the polycyclic framework of the natural product." @default.
- W2800247243 created "2018-05-17" @default.
- W2800247243 creator A5020332614 @default.
- W2800247243 creator A5038661637 @default.
- W2800247243 creator A5053270056 @default.
- W2800247243 creator A5065968919 @default.
- W2800247243 creator A5077428547 @default.
- W2800247243 date "2018-05-04" @default.
- W2800247243 modified "2023-10-14" @default.
- W2800247243 title "Evolution of a Strategy for the Enantioselective Total Synthesis of (+)-Psiguadial B" @default.
- W2800247243 cites W1905486867 @default.
- W2800247243 cites W1966122995 @default.
- W2800247243 cites W1967084324 @default.
- W2800247243 cites W1968896254 @default.
- W2800247243 cites W1981055366 @default.
- W2800247243 cites W1983257620 @default.
- W2800247243 cites W1983413735 @default.
- W2800247243 cites W1990105855 @default.
- W2800247243 cites W1993418415 @default.
- W2800247243 cites W1994390276 @default.
- W2800247243 cites W1996922791 @default.
- W2800247243 cites W1997534644 @default.
- W2800247243 cites W2001471487 @default.
- W2800247243 cites W2001938798 @default.
- W2800247243 cites W2002068050 @default.
- W2800247243 cites W2003577473 @default.
- W2800247243 cites W2003881863 @default.
- W2800247243 cites W2004717010 @default.
- W2800247243 cites W2011592968 @default.
- W2800247243 cites W2013096298 @default.
- W2800247243 cites W2018584158 @default.
- W2800247243 cites W2019175970 @default.
- W2800247243 cites W2019634345 @default.
- W2800247243 cites W2026049307 @default.
- W2800247243 cites W2026749398 @default.
- W2800247243 cites W2027105561 @default.
- W2800247243 cites W2028310662 @default.
- W2800247243 cites W2028995357 @default.
- W2800247243 cites W2030698387 @default.
- W2800247243 cites W2031184064 @default.
- W2800247243 cites W2037032992 @default.
- W2800247243 cites W2037043173 @default.
- W2800247243 cites W2037844373 @default.
- W2800247243 cites W2039020897 @default.
- W2800247243 cites W2040402824 @default.
- W2800247243 cites W2040884478 @default.
- W2800247243 cites W2043880875 @default.
- W2800247243 cites W2046951148 @default.
- W2800247243 cites W2050903553 @default.
- W2800247243 cites W2053773972 @default.
- W2800247243 cites W2055587019 @default.
- W2800247243 cites W2056730143 @default.
- W2800247243 cites W2058539240 @default.
- W2800247243 cites W2059075666 @default.
- W2800247243 cites W2065120302 @default.
- W2800247243 cites W2069257958 @default.
- W2800247243 cites W2069607377 @default.
- W2800247243 cites W2070931279 @default.
- W2800247243 cites W2073262613 @default.
- W2800247243 cites W2074960707 @default.
- W2800247243 cites W2077538531 @default.
- W2800247243 cites W2077801201 @default.
- W2800247243 cites W2081356085 @default.
- W2800247243 cites W2082991625 @default.
- W2800247243 cites W2084761587 @default.
- W2800247243 cites W2087459593 @default.
- W2800247243 cites W2089245494 @default.
- W2800247243 cites W2090073484 @default.
- W2800247243 cites W2092609702 @default.
- W2800247243 cites W2093977680 @default.
- W2800247243 cites W2094269209 @default.
- W2800247243 cites W2095120464 @default.
- W2800247243 cites W2097186155 @default.
- W2800247243 cites W2099534742 @default.
- W2800247243 cites W2100146724 @default.
- W2800247243 cites W2102732628 @default.
- W2800247243 cites W2105657496 @default.
- W2800247243 cites W2108847394 @default.
- W2800247243 cites W2110157790 @default.
- W2800247243 cites W2110170720 @default.
- W2800247243 cites W2111034257 @default.
- W2800247243 cites W2113616352 @default.
- W2800247243 cites W2115785328 @default.
- W2800247243 cites W2118543400 @default.
- W2800247243 cites W2125201710 @default.
- W2800247243 cites W2128767765 @default.
- W2800247243 cites W2132611443 @default.
- W2800247243 cites W2133842906 @default.
- W2800247243 cites W2135695529 @default.
- W2800247243 cites W2138023898 @default.
- W2800247243 cites W2141572176 @default.
- W2800247243 cites W2144882695 @default.
- W2800247243 cites W2145633882 @default.
- W2800247243 cites W2145856813 @default.
- W2800247243 cites W2146686359 @default.
- W2800247243 cites W2154525274 @default.
- W2800247243 cites W2154721342 @default.
- W2800247243 cites W2159897767 @default.