Total synthesis of aristolactam alkaloids via synergistic C-H bond activation and dehydro-Diels-Alder reactions

Chemical Science
Mallu Chenna Reddy, Masilamani Jeganmohan

Abstract

A concise total synthesis of aristolactam alkaloids by a synergistic combination of C-H bond activation and dehydro-Diels-Alder reactions is described. To achieve the synthesis two new synthetic methodologies, namely the oxidative cyclization of benzamides with vinyl sulfone leading to 3-methyleneisoindolin-1-ones via a ruthenium-catalyzed C-H bond activation, and a dehydro-Diels-Alder reaction followed by the fluoride ion mediated desulfonylation of 3-methyleneisoindolin-1-ones with benzynes, were developed. The method presented allows the opportunity for the construction of all the rings of aristolactams from easily available starting materials.

References

Jan 1, 1987·Toxicon : Official Journal of the International Society on Toxinology·B S Vishwanath, T V Gowda
Nov 28, 2001·The Journal of Organic Chemistry·C HoarauP Grandclaudon
Jan 17, 2002·Archives of Pharmacal Research·S K KimY S Kim
Feb 12, 2005·The Journal of Organic Chemistry·Tuanli Yao, Richard C Larock
Jun 3, 2006·Natural Product Reports·Kenneth W Bentley
Nov 28, 2008·Journal of the American Chemical Society·Kevin M Allan, Brian M Stoltz
Apr 28, 2009·Bioorganic & Medicinal Chemistry Letters·Young Lok ChoiJung-Nyoung Heo
May 15, 2009·Chemical Reviews·Denise A ColbyJonathan A Ellman
Jan 19, 2010·Chemical Reviews·Thomas W Lyons, Melanie S Sanford
Apr 3, 2010·Journal of the American Chemical Society·Yi LuJin-Quan Yu
Aug 27, 2010·Chemistry : a European Journal·Tetsuya Satoh, Masahiro Miura
Jan 27, 2011·Angewandte Chemie·Frederic W PatureauFrank Glorius
Mar 12, 2011·Chemical Reviews·Jean Le Bras, Jacques Muzart
May 25, 2011·Journal of the American Chemical Society·Emmanuel Ferrer FlegeauAnny Jutand
Sep 14, 2011·Organic Letters·Joe W WrigglesworthKevin I Booker-Milburn
Nov 2, 2011·Organic Letters·Kishor Padala, Masilamani Jeganmohan
Nov 4, 2011·Chemical Communications : Chem Comm·Dan-Dan LiGuan-Wu Wang
Dec 15, 2011·Accounts of Chemical Research·Keary M EngleJin-Quan Yu
Mar 17, 2012·Angewandte Chemie·Christian M Gampe, Erick M Carreira
Mar 27, 2012·Chemical Reviews·Pamela M Tadross, Brian M Stoltz
Apr 12, 2012·Chemistry, an Asian Journal·Chen ZhuJohn R Falck
Jun 22, 2012·Organic & Biomolecular Chemistry·Xiaohong WeiXingwei Li
Aug 10, 2012·Organic Letters·Krishnamoorthy MuralirajanChien-Hong Cheng
Sep 1, 2012·Chemical Reviews·Percia Beatrice ArockiamPierre H Dixneuf
Oct 13, 2012·Nature·Thomas R HoyeBrian P Woods
Dec 19, 2012·Nature Chemistry·Adam E Goetz, Neil K Garg
Jan 29, 2014·The Journal of Organic Chemistry·Hai Xiao SiyangPei Nian Liu
Apr 3, 2014·Natural Product Reports·Johanna MichlMichael Heinrich
Oct 11, 2014·Journal of the American Chemical Society·Jose M MedinaK N Houk
Jan 13, 2015·Chemistry, an Asian Journal·Parthasarathy Gandeepan, Chien-Hong Cheng
Jan 15, 2015·Chemical Communications : Chem Comm·Ramasamy Manoharan, Masilamani Jeganmohan
Sep 17, 2015·The Journal of Organic Chemistry·Allan F C RossiniCristiano Raminelli

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Citations

Oct 26, 2018·Chemical Society Reviews·Hiroshi TakikawaKeisuke Suzuki
Apr 21, 2018·Organic & Biomolecular Chemistry·Arumugam MariappanMasilamani Jeganmohan
Aug 20, 2020·Chemistry : a European Journal·Trisha Banik, Krishna P Kaliappan
Jan 20, 2021·Organic Letters·Ravichandran Logeswaran, Masilamani Jeganmohan
Oct 31, 2020·Chemistry : a European Journal·Risto Savela, Carolina Méndez-Gálvez
Feb 19, 2021·Chemical Reviews·Jiarong ShiYang Li
Jun 2, 2021·Organic Letters·Chikkabagilu Nagaraju Shambhavi, Masilamani Jeganmohan
Jun 25, 2021·Chemical Science·Wajid AliDebabrata Maiti
Mar 2, 2019·The Journal of Organic Chemistry·Ramakrishnan SivasakthikumaranMasilamani Jeganmohan
Aug 17, 2021·Chemical Communications : Chem Comm·Bhargav DesaiTogati Naveen
Mar 3, 2018·The Journal of Organic Chemistry·Masilamani TamizmaniMasilamani Jeganmohan
May 26, 2018·The Journal of Organic Chemistry·Adapa AnukumarMasilamani Jeganmohan
Nov 11, 2021·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Tamiris R C SilvaCristiano Raminelli

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