Matches in SemOpenAlex for { <https://semopenalex.org/work/W2059693880> ?p ?o ?g. }
- W2059693880 endingPage "10762" @default.
- W2059693880 startingPage "10747" @default.
- W2059693880 abstract "The asymmetric total synthesis of lagunamide A (3.0%, 20 steps longest linear sequence) and its five analogues, including the structure dehydrated at the C37 position, are detailed in this report. The key feature in this diverse synthesis includes the elaboration of four consecutive chiral centers at C37–40 and the final macrocyclization. Starting from chiral aldehyde 10, we synthesized both 1,3-anti and 1,3-syn homoallylic alcohols 20a and 20b through asymmetric aldol condensation and stereoselective allylation. The following esterification to introduce the l-N-Me-Ala unit resulted in significant epimerization. This problem was finally overcome by coupling the alcohols with the corresponding acid chloride of the l-alanine derivative. The key α,β-unsaturated carboxylic acid unit was produced by cross-metathesis (CM) of methacrylaldehyde and related olefins. Interestingly, we found that the C7 configuration dramatically affected the ring closure. Natural lagunamide A (1a), its 39-epimer (1c), and its 2-epimer (1d) were obtained through macrolactamization between alanine and isoleucine moieties." @default.
- W2059693880 created "2016-06-24" @default.
- W2059693880 creator A5007661741 @default.
- W2059693880 creator A5044450373 @default.
- W2059693880 creator A5047402842 @default.
- W2059693880 creator A5047533857 @default.
- W2059693880 creator A5072247998 @default.
- W2059693880 date "2013-10-23" @default.
- W2059693880 modified "2023-10-07" @default.
- W2059693880 title "Diverse Synthesis of Marine Cyclic Depsipeptide Lagunamide A and Its Analogues" @default.
- W2059693880 cites W1966293351 @default.
- W2059693880 cites W1968436252 @default.
- W2059693880 cites W1970122262 @default.
- W2059693880 cites W1970264509 @default.
- W2059693880 cites W1971910884 @default.
- W2059693880 cites W1977121059 @default.
- W2059693880 cites W1979034677 @default.
- W2059693880 cites W1989350409 @default.
- W2059693880 cites W1991700756 @default.
- W2059693880 cites W1994162165 @default.
- W2059693880 cites W1995647974 @default.
- W2059693880 cites W1997867296 @default.
- W2059693880 cites W2001301872 @default.
- W2059693880 cites W2003323698 @default.
- W2059693880 cites W2004836957 @default.
- W2059693880 cites W2013560158 @default.
- W2059693880 cites W2015127993 @default.
- W2059693880 cites W2016981590 @default.
- W2059693880 cites W2017719613 @default.
- W2059693880 cites W2022412731 @default.
- W2059693880 cites W2024269666 @default.
- W2059693880 cites W2025609508 @default.
- W2059693880 cites W2031598870 @default.
- W2059693880 cites W2032603070 @default.
- W2059693880 cites W2034054515 @default.
- W2059693880 cites W2041084364 @default.
- W2059693880 cites W2042085220 @default.
- W2059693880 cites W2044568919 @default.
- W2059693880 cites W2049785359 @default.
- W2059693880 cites W2050781056 @default.
- W2059693880 cites W2052375666 @default.
- W2059693880 cites W2052545303 @default.
- W2059693880 cites W2055718243 @default.
- W2059693880 cites W2058100982 @default.
- W2059693880 cites W2058623521 @default.
- W2059693880 cites W2062735328 @default.
- W2059693880 cites W2064408085 @default.
- W2059693880 cites W2064912418 @default.
- W2059693880 cites W2066821030 @default.
- W2059693880 cites W2067573017 @default.
- W2059693880 cites W2070593611 @default.
- W2059693880 cites W2076947283 @default.
- W2059693880 cites W2079620945 @default.
- W2059693880 cites W2086143127 @default.
- W2059693880 cites W2096916334 @default.
- W2059693880 cites W2101562788 @default.
- W2059693880 cites W2104516185 @default.
- W2059693880 cites W2120214883 @default.
- W2059693880 cites W2140761602 @default.
- W2059693880 cites W2167529420 @default.
- W2059693880 cites W2171994385 @default.
- W2059693880 cites W2178088651 @default.
- W2059693880 cites W2326454402 @default.
- W2059693880 cites W2327841955 @default.
- W2059693880 cites W2951407685 @default.
- W2059693880 cites W2953231399 @default.
- W2059693880 cites W4231644331 @default.
- W2059693880 doi "https://doi.org/10.1021/jo401687s" @default.
- W2059693880 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/24090274" @default.
- W2059693880 hasPublicationYear "2013" @default.
- W2059693880 type Work @default.
- W2059693880 sameAs 2059693880 @default.
- W2059693880 citedByCount "43" @default.
- W2059693880 countsByYear W20596938802014 @default.
- W2059693880 countsByYear W20596938802015 @default.
- W2059693880 countsByYear W20596938802016 @default.
- W2059693880 countsByYear W20596938802017 @default.
- W2059693880 countsByYear W20596938802018 @default.
- W2059693880 countsByYear W20596938802020 @default.
- W2059693880 countsByYear W20596938802021 @default.
- W2059693880 countsByYear W20596938802022 @default.
- W2059693880 countsByYear W20596938802023 @default.
- W2059693880 crossrefType "journal-article" @default.
- W2059693880 hasAuthorship W2059693880A5007661741 @default.
- W2059693880 hasAuthorship W2059693880A5044450373 @default.
- W2059693880 hasAuthorship W2059693880A5047402842 @default.
- W2059693880 hasAuthorship W2059693880A5047533857 @default.
- W2059693880 hasAuthorship W2059693880A5072247998 @default.
- W2059693880 hasConcept C106159729 @default.
- W2059693880 hasConcept C111771559 @default.
- W2059693880 hasConcept C146686406 @default.
- W2059693880 hasConcept C153914509 @default.
- W2059693880 hasConcept C161790260 @default.
- W2059693880 hasConcept C162324750 @default.
- W2059693880 hasConcept C168831097 @default.
- W2059693880 hasConcept C178790620 @default.
- W2059693880 hasConcept C181647583 @default.
- W2059693880 hasConcept C185592680 @default.