Synthesis, Table of Contents SHORTPAPER © Georg Thieme Verlag Stuttgart · New York A Facile Synthesis of Rubrolide E [1] Anirban Kar, Narshinha P. Argade*Division of Organic Chemistry (Synthesis), National Chemical Laboratory, Pune 411 008, IndiaFax: +91(20)25893153; e-Mail: argade@dalton.ncl.res.in; Recommend Article Abstract Buy Article All articles of this category Abstract A simple and efficient synthesis of rubrolide E (1e) has been demonstrated via Meerwein coupling reaction of para-anisyldiazonium chloride with N-phenylmaleimide (2), regioselective reduction of para-anisylmaleic anhydride (4), Knoevenagel condensation of butyrolactone 5 with para-anisaldehyde and demethylation pathway. Key words N-phenylmaleimide - Meerwein coupling - regioselective reduction - Knoevenagel condensation - rubrolide E - total synthesis Full Text References References1 NCL Communication No. 6680. 2a Rao YS. Chem. Rev. 1976, 76: 625 2b Pattenden G. Fortschr. Chem. Org. Naturst. 1978, 35: 133 2c Bernard W. Pure Appl. Chem. 1997, 69: 627 2d Negishi E. Kotora M. Tetrahedron 1997, 53: 6707 2e Tan L. Chen C.-Y. Larsen RD. Verhoeven TR. Reider PJ. Tetrahedron Lett. 1998, 39: 3961 2f Sakuda S. Yamada Y. Compr. Nat. Prod. Chem. 1999, 1: 139 ; and references cited therein 3 Miao S. Andersen RJ. J. Org. Chem. 1991, 56: 6275 4 Ortega MJ. Zubia E. Ocana JM. Naranjo S. Salva J. Tetrahedron 2000, 56: 3963 5a Kotora M. Negishi E. Synthesis 1997, 121 5b Boukouvalas J. Lachance N. Ouellet M. Trudeau M. Tetrahedron Lett. 1998, 39: 7665 5c Prim D. Fuss A. Kirsch G. Silva AMS. J. Chem. Soc., Perkin Trans. 2 1999, 1175 5d Bellina F. Anselmi C. Stephane V. Mannina L. Rossi R. Tetrahedron 2001, 57: 9997 5e Bellina F. Anselmi C. Rossi R. Tetrahedron Lett. 2002, 43: 2023 5f Bellina F. Anselmi C. Martina F. Rossi R. Eur. J. Org. Chem. 2003, 2290 5g Boukouvalas J. Pouliot M. Synlett 2005, 343 ; and references cited therein 6a Gogoi S. Argade NP. Tetrahedron 2004, 60: 9093 6b Mondal M. Argade NP. Tetrahedron Lett. 2004, 45: 5693 6c Mondal M. Argade NP. Synlett 2004, 1243 6d Mangaleswaran S. Argade NP. Synthesis 2004, 1560 6e Mhaske SB. Argade NP. Tetrahedron 2004, 60: 3417 6f Argade NP. Balasubramaniyan V. Heterocycles 2000, 53: 475 ; and references cited therein 7 Rondestvedt CS. Vogl O. J. Am. Chem. Soc. 1955, 77: 2313
