Matches in SemOpenAlex for { <https://semopenalex.org/work/W1998131271> ?p ?o ?g. }
- W1998131271 endingPage "7607" @default.
- W1998131271 startingPage "7592" @default.
- W1998131271 abstract "A formal synthesis of didehydrostemofoline and isodidehydrostemofoline has been accomplished by preparing an intermediate in the Overman synthesis of these alkaloids from commercially available 2-deoxy-D-ribose. The work presented in this account chronicles the evolution of our explorations to identify the optimal steric and electronic control elements necessary to generate the tricyclic core structure of these alkaloids in a single operation from an acyclic precursor. The key step in the synthesis is a novel dipolar cycloaddition cascade sequence that is initiated by cyclization of a rhodium-derived carbene onto the nitrogen atom of a proximal imine group to generate an azomethine ylide that then undergoes spontaneous cyclization via dipolar cycloaddition. The synthesis features several other interesting reactions, including a Boord elimination to prepare a chiral allylic alcohol, a highly diastereoselective Hirama-Itô cyclization, and a useful modification of the Barton decarboxylation protocol." @default.
- W1998131271 created "2016-06-24" @default.
- W1998131271 creator A5042479736 @default.
- W1998131271 creator A5055989647 @default.
- W1998131271 creator A5064695481 @default.
- W1998131271 creator A5068590696 @default.
- W1998131271 date "2013-09-01" @default.
- W1998131271 modified "2023-10-09" @default.
- W1998131271 title "Asymmetric formal total synthesis of the stemofoline alkaloids: the evolution, development, and application of a catalytic dipolar cycloaddition cascade" @default.
- W1998131271 cites W1964370801 @default.
- W1998131271 cites W1964977558 @default.
- W1998131271 cites W1967138821 @default.
- W1998131271 cites W1969874059 @default.
- W1998131271 cites W1974671081 @default.
- W1998131271 cites W1976878228 @default.
- W1998131271 cites W1978254166 @default.
- W1998131271 cites W1979299241 @default.
- W1998131271 cites W1985920312 @default.
- W1998131271 cites W1991628375 @default.
- W1998131271 cites W1992829864 @default.
- W1998131271 cites W1993111639 @default.
- W1998131271 cites W1993291457 @default.
- W1998131271 cites W1998336349 @default.
- W1998131271 cites W1998942506 @default.
- W1998131271 cites W2000703876 @default.
- W1998131271 cites W2002452153 @default.
- W1998131271 cites W2007862406 @default.
- W1998131271 cites W2008125618 @default.
- W1998131271 cites W2008520613 @default.
- W1998131271 cites W2008547736 @default.
- W1998131271 cites W2009491154 @default.
- W1998131271 cites W2013886932 @default.
- W1998131271 cites W2014613303 @default.
- W1998131271 cites W2018018488 @default.
- W1998131271 cites W2020373423 @default.
- W1998131271 cites W2022518839 @default.
- W1998131271 cites W2023065487 @default.
- W1998131271 cites W2023506524 @default.
- W1998131271 cites W2025752792 @default.
- W1998131271 cites W2026812670 @default.
- W1998131271 cites W2035701354 @default.
- W1998131271 cites W2036457071 @default.
- W1998131271 cites W2041050033 @default.
- W1998131271 cites W2049111974 @default.
- W1998131271 cites W2063023861 @default.
- W1998131271 cites W2064220822 @default.
- W1998131271 cites W2065331068 @default.
- W1998131271 cites W2067030782 @default.
- W1998131271 cites W2069607377 @default.
- W1998131271 cites W2072919769 @default.
- W1998131271 cites W2074696763 @default.
- W1998131271 cites W2082580834 @default.
- W1998131271 cites W2084401698 @default.
- W1998131271 cites W2084986551 @default.
- W1998131271 cites W2086499177 @default.
- W1998131271 cites W2089582836 @default.
- W1998131271 cites W2093822992 @default.
- W1998131271 cites W2104299063 @default.
- W1998131271 cites W2106402584 @default.
- W1998131271 cites W2129746707 @default.
- W1998131271 cites W2130276904 @default.
- W1998131271 cites W2148561916 @default.
- W1998131271 cites W2148819995 @default.
- W1998131271 cites W2152023007 @default.
- W1998131271 cites W2157081904 @default.
- W1998131271 cites W2171719775 @default.
- W1998131271 cites W2319648046 @default.
- W1998131271 cites W2320246526 @default.
- W1998131271 cites W2949544641 @default.
- W1998131271 cites W2949635548 @default.
- W1998131271 cites W2949660517 @default.
- W1998131271 cites W2949899443 @default.
- W1998131271 cites W2949936034 @default.
- W1998131271 cites W2950160551 @default.
- W1998131271 cites W2950718566 @default.
- W1998131271 cites W2950777055 @default.
- W1998131271 cites W2950859886 @default.
- W1998131271 cites W2951556393 @default.
- W1998131271 cites W2952027929 @default.
- W1998131271 cites W2952061839 @default.
- W1998131271 cites W2952501699 @default.
- W1998131271 cites W2953071791 @default.
- W1998131271 cites W2953091442 @default.
- W1998131271 cites W4230608042 @default.
- W1998131271 cites W4243517572 @default.
- W1998131271 doi "https://doi.org/10.1016/j.tet.2013.03.104" @default.
- W1998131271 hasPubMedCentralId "https://www.ncbi.nlm.nih.gov/pmc/articles/3780458" @default.
- W1998131271 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/24072939" @default.
- W1998131271 hasPublicationYear "2013" @default.
- W1998131271 type Work @default.
- W1998131271 sameAs 1998131271 @default.
- W1998131271 citedByCount "18" @default.
- W1998131271 countsByYear W19981312712015 @default.
- W1998131271 countsByYear W19981312712016 @default.
- W1998131271 countsByYear W19981312712017 @default.
- W1998131271 countsByYear W19981312712018 @default.
- W1998131271 countsByYear W19981312712020 @default.
- W1998131271 countsByYear W19981312712021 @default.