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- W1964719724 abstract "A highly stereocontrolled total synthesis of the 18-membered macrolide (+)-concanamycin F, a potent inhibitor of vacuolar ATPases, is described that proceeds in 5.8% yield over 26 steps. The three key fragments, C1–C13 vinyl iodide, C14–C22 vinyl stannane and C23–C28 aldehyde, were efficiently constructed using asymmetric boron-mediated aldol reactions of appropriate chiral ketone building blocks. The nature of the silyl protection of the C7/C9 hydroxyls proved to be critical for achieving macrocyclisation, with TES ethers being superior to a cyclic silylene derivative. Following a Liebeskind-Stille cross-coupling reaction between the C1–C13 vinyl iodide and C14–C22 vinyl stannane fragments to assemble the (12E,14E)-diene, a modified Yamaguchi macrolactonisation delivered the requisite 18-membered macrocyclic core. This advanced intermediate was also obtained by an alternative sequence using an esterification step to connect the C1–C13 and C14–C22 fragments followed by a Pd-catalysed intramolecular Stille reaction to install the (12E,14E)-diene. Conversion of the resulting macrocyclic intermediate into a methyl ketone then enabled a highly diastereoselective Mukaiyama aldol coupling of the derived silyl enol ether with the C13–C28 aldehyde fragment to install the fully elaborated side chain, whereby subsequent global deprotection of the resulting β-hydroxyketone under suitable conditions (TASF followed by p-TsOH) afforded (+)-concanamycin F." @default.
- W1964719724 created "2016-06-24" @default.
- W1964719724 creator A5016051848 @default.
- W1964719724 creator A5042164708 @default.
- W1964719724 creator A5071896609 @default.
- W1964719724 creator A5087092097 @default.
- W1964719724 date "2011-12-01" @default.
- W1964719724 modified "2023-10-09" @default.
- W1964719724 title "Stereocontrolled total synthesis of (+)-concanamycin F: the strategic use of boron-mediated aldol reactions of chiral ketones" @default.
- W1964719724 cites W1943839210 @default.
- W1964719724 cites W1963809796 @default.
- W1964719724 cites W1966391082 @default.
- W1964719724 cites W1967696920 @default.
- W1964719724 cites W1969645612 @default.
- W1964719724 cites W1971337354 @default.
- W1964719724 cites W1972295774 @default.
- W1964719724 cites W1974066200 @default.
- W1964719724 cites W1979839917 @default.
- W1964719724 cites W1980703290 @default.
- W1964719724 cites W1980947232 @default.
- W1964719724 cites W1981130165 @default.
- W1964719724 cites W1984168496 @default.
- W1964719724 cites W1988354257 @default.
- W1964719724 cites W2001890870 @default.
- W1964719724 cites W2003334359 @default.
- W1964719724 cites W2006176190 @default.
- W1964719724 cites W2009982693 @default.
- W1964719724 cites W2010871897 @default.
- W1964719724 cites W2011822328 @default.
- W1964719724 cites W2013729033 @default.
- W1964719724 cites W2013998077 @default.
- W1964719724 cites W2018231472 @default.
- W1964719724 cites W2022412731 @default.
- W1964719724 cites W2023550796 @default.
- W1964719724 cites W2024122111 @default.
- W1964719724 cites W2024344970 @default.
- W1964719724 cites W2024792329 @default.
- W1964719724 cites W2030653721 @default.
- W1964719724 cites W2031684845 @default.
- W1964719724 cites W2035501441 @default.
- W1964719724 cites W2036931279 @default.
- W1964719724 cites W2039660403 @default.
- W1964719724 cites W2041983611 @default.
- W1964719724 cites W2045115741 @default.
- W1964719724 cites W2045171105 @default.
- W1964719724 cites W2045948166 @default.
- W1964719724 cites W2046148051 @default.
- W1964719724 cites W2047374854 @default.
- W1964719724 cites W2054378884 @default.
- W1964719724 cites W2056138506 @default.
- W1964719724 cites W2057628256 @default.
- W1964719724 cites W2058950432 @default.
- W1964719724 cites W2060912642 @default.
- W1964719724 cites W2063081431 @default.
- W1964719724 cites W2066278849 @default.
- W1964719724 cites W2066864448 @default.
- W1964719724 cites W2067573017 @default.
- W1964719724 cites W2071098418 @default.
- W1964719724 cites W2074632092 @default.
- W1964719724 cites W2075171546 @default.
- W1964719724 cites W2087304241 @default.
- W1964719724 cites W2089608000 @default.
- W1964719724 cites W2091102942 @default.
- W1964719724 cites W2091243736 @default.
- W1964719724 cites W2093142684 @default.
- W1964719724 cites W2095880819 @default.
- W1964719724 cites W2096535122 @default.
- W1964719724 cites W2107842389 @default.
- W1964719724 cites W2116969142 @default.
- W1964719724 cites W2119593149 @default.
- W1964719724 cites W2121755458 @default.
- W1964719724 cites W2125006413 @default.
- W1964719724 cites W2135193488 @default.
- W1964719724 cites W2157987891 @default.
- W1964719724 cites W2160331845 @default.
- W1964719724 cites W2164173822 @default.
- W1964719724 cites W2313908369 @default.
- W1964719724 cites W2326817151 @default.
- W1964719724 cites W2614123444 @default.
- W1964719724 cites W2949503906 @default.
- W1964719724 cites W2949725887 @default.
- W1964719724 cites W2951021862 @default.
- W1964719724 cites W2951114239 @default.
- W1964719724 cites W2951343589 @default.
- W1964719724 cites W2951405879 @default.
- W1964719724 cites W2951407685 @default.
- W1964719724 cites W2952488379 @default.
- W1964719724 cites W2952967879 @default.
- W1964719724 cites W4235729092 @default.
- W1964719724 cites W82364718 @default.
- W1964719724 doi "https://doi.org/10.1016/j.tet.2011.09.012" @default.
- W1964719724 hasPublicationYear "2011" @default.
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