Matches in SemOpenAlex for { <https://semopenalex.org/work/W2004366916> ?p ?o ?g. }
- W2004366916 endingPage "9074" @default.
- W2004366916 startingPage "9065" @default.
- W2004366916 abstract "Addition of guanidine to a 6-methylhexahydroindenone in MeOH at 85 °C afforded 7-epineoptilocaulin. A similar reaction with a 6-propylhexahydroindenone afforded netamine E. MnO2 oxidation of 7-epineoptilocaulin and netamine E afforded mirabilin B and netamine G, respectively. The netamines have the side chains trans, not cis as was initially proposed. A unified biosynthetic scheme for the batzelladines and ptilocaulin family is proposed. Conjugate addition of guanidine to a bis enone followed by an intramolecular Michael reaction of the enolate to the other enone, aldol reaction, dehydration, and enamine formation will lead to a tricyclic intermediate at the dehydroptilocaulin oxidation state. 1,4-Hydride addition will lead to ptilocaulin or 7-epineoptilocaulin depending on which face the hydride adds to. 1,2-Hydride addition will lead to isoptilocaulin. The key tricyclic intermediate was prepared from a tetrahydroindenone and guanidine and reduced with NaBH4 to give a mixture rich in ptilocaulin and isoptilocaulin." @default.
- W2004366916 created "2016-06-24" @default.
- W2004366916 creator A5041353759 @default.
- W2004366916 creator A5063057227 @default.
- W2004366916 creator A5086583228 @default.
- W2004366916 date "2008-10-18" @default.
- W2004366916 modified "2023-10-10" @default.
- W2004366916 title "Synthesis of 7-Epineoptilocaulin, Mirabilin B, and Isoptilocaulin. A Unified Biosynthetic Proposal for the Ptilocaulin and Batzelladine Alkaloids. Synthesis and Structure Revision of Netamines E and G" @default.
- W2004366916 cites W1970862953 @default.
- W2004366916 cites W1973315486 @default.
- W2004366916 cites W1977042516 @default.
- W2004366916 cites W1977274816 @default.
- W2004366916 cites W1977799153 @default.
- W2004366916 cites W1978458510 @default.
- W2004366916 cites W1978859970 @default.
- W2004366916 cites W1980543039 @default.
- W2004366916 cites W1990585247 @default.
- W2004366916 cites W1991530434 @default.
- W2004366916 cites W1993639443 @default.
- W2004366916 cites W1995631361 @default.
- W2004366916 cites W1999399550 @default.
- W2004366916 cites W2004170980 @default.
- W2004366916 cites W2004925737 @default.
- W2004366916 cites W2005713155 @default.
- W2004366916 cites W2015303610 @default.
- W2004366916 cites W2017066643 @default.
- W2004366916 cites W2017806818 @default.
- W2004366916 cites W2022495507 @default.
- W2004366916 cites W2023722348 @default.
- W2004366916 cites W2027600668 @default.
- W2004366916 cites W2027884537 @default.
- W2004366916 cites W2030298156 @default.
- W2004366916 cites W2038035400 @default.
- W2004366916 cites W2046143876 @default.
- W2004366916 cites W2050422302 @default.
- W2004366916 cites W2051641068 @default.
- W2004366916 cites W2057424916 @default.
- W2004366916 cites W2061359141 @default.
- W2004366916 cites W2065784908 @default.
- W2004366916 cites W2067064862 @default.
- W2004366916 cites W2074520200 @default.
- W2004366916 cites W2077967501 @default.
- W2004366916 cites W2079948746 @default.
- W2004366916 cites W2085009812 @default.
- W2004366916 cites W2087186658 @default.
- W2004366916 cites W2091388781 @default.
- W2004366916 cites W2092186216 @default.
- W2004366916 cites W2128417309 @default.
- W2004366916 cites W2140507921 @default.
- W2004366916 cites W2150188019 @default.
- W2004366916 cites W2154897072 @default.
- W2004366916 cites W2166990621 @default.
- W2004366916 cites W2329072683 @default.
- W2004366916 cites W2949452828 @default.
- W2004366916 cites W2950732851 @default.
- W2004366916 cites W2951412372 @default.
- W2004366916 cites W2951915785 @default.
- W2004366916 cites W2952143506 @default.
- W2004366916 cites W2953000299 @default.
- W2004366916 cites W3004801057 @default.
- W2004366916 cites W4236375831 @default.
- W2004366916 cites W4243566768 @default.
- W2004366916 cites W4250812124 @default.
- W2004366916 cites W4321429216 @default.
- W2004366916 doi "https://doi.org/10.1021/jo801956w" @default.
- W2004366916 hasPubMedCentralId "https://www.ncbi.nlm.nih.gov/pmc/articles/2593083" @default.
- W2004366916 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/18928319" @default.
- W2004366916 hasPublicationYear "2008" @default.
- W2004366916 type Work @default.
- W2004366916 sameAs 2004366916 @default.
- W2004366916 citedByCount "41" @default.
- W2004366916 countsByYear W20043669162012 @default.
- W2004366916 countsByYear W20043669162013 @default.
- W2004366916 countsByYear W20043669162014 @default.
- W2004366916 countsByYear W20043669162015 @default.
- W2004366916 countsByYear W20043669162017 @default.
- W2004366916 countsByYear W20043669162018 @default.
- W2004366916 countsByYear W20043669162019 @default.
- W2004366916 countsByYear W20043669162021 @default.
- W2004366916 countsByYear W20043669162022 @default.
- W2004366916 crossrefType "journal-article" @default.
- W2004366916 hasAuthorship W2004366916A5041353759 @default.
- W2004366916 hasAuthorship W2004366916A5063057227 @default.
- W2004366916 hasAuthorship W2004366916A5086583228 @default.
- W2004366916 hasBestOaLocation W20043669162 @default.
- W2004366916 hasConcept C112423150 @default.
- W2004366916 hasConcept C134306372 @default.
- W2004366916 hasConcept C161790260 @default.
- W2004366916 hasConcept C178790620 @default.
- W2004366916 hasConcept C185592680 @default.
- W2004366916 hasConcept C18616679 @default.
- W2004366916 hasConcept C197336794 @default.
- W2004366916 hasConcept C2776378156 @default.
- W2004366916 hasConcept C2777961443 @default.
- W2004366916 hasConcept C2779463914 @default.
- W2004366916 hasConcept C2779746879 @default.
- W2004366916 hasConcept C33923547 @default.
- W2004366916 hasConcept C544153396 @default.