Synthesis, Inhaltsverzeichnis SHORTPAPER© Georg Thieme Verlag Stuttgart · New YorkA 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; Artikel empfehlen Abstract Artikel einzeln kaufen Alle Artikel dieser Rubrik 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 Volltext Referenzen References<A NAME="RZ04905SS-1">1</A> NCL Communication No. 6680. <A NAME="RZ04905SS-2A">2a</A> Rao YS. Chem. Rev. 1976, 76: 625 <A NAME="RZ04905SS-2B">2b</A> Pattenden G. Fortschr. Chem. Org. Naturst. 1978, 35: 133 <A NAME="RZ04905SS-2C">2c</A> Bernard W. Pure Appl. Chem. 1997, 69: 627 <A NAME="RZ04905SS-2D">2d</A> Negishi E. Kotora M. Tetrahedron 1997, 53: 6707 <A NAME="RZ04905SS-2E">2e</A> Tan L. Chen C.-Y. Larsen RD. Verhoeven TR. Reider PJ. Tetrahedron Lett. 1998, 39: 3961 <A NAME="RZ04905SS-2F">2f</A> Sakuda S. Yamada Y. Compr. Nat. Prod. Chem. 1999, 1: 139 ; and references cited therein <A NAME="RZ04905SS-3">3</A> Miao S. Andersen RJ. J. Org. Chem. 1991, 56: 6275 <A NAME="RZ04905SS-4">4</A> Ortega MJ. Zubia E. Ocana JM. Naranjo S. Salva J. Tetrahedron 2000, 56: 3963 <A NAME="RZ04905SS-5A">5a</A> Kotora M. Negishi E. Synthesis 1997, 121 <A NAME="RZ04905SS-5B">5b</A> Boukouvalas J. Lachance N. Ouellet M. Trudeau M. Tetrahedron Lett. 1998, 39: 7665 <A NAME="RZ04905SS-5C">5c</A> Prim D. Fuss A. Kirsch G. Silva AMS. J. Chem. Soc., Perkin Trans. 2 1999, 1175 <A NAME="RZ04905SS-5D">5d</A> Bellina F. Anselmi C. Stephane V. Mannina L. Rossi R. Tetrahedron 2001, 57: 9997 <A NAME="RZ04905SS-5E">5e</A> Bellina F. Anselmi C. Rossi R. Tetrahedron Lett. 2002, 43: 2023 <A NAME="RZ04905SS-5F">5f</A> Bellina F. Anselmi C. Martina F. Rossi R. Eur. J. Org. Chem. 2003, 2290 <A NAME="RZ04905SS-5G">5g</A> Boukouvalas J. Pouliot M. Synlett 2005, 343 ; and references cited therein <A NAME="RZ04905SS-6A">6a</A> Gogoi S. Argade NP. Tetrahedron 2004, 60: 9093 <A NAME="RZ04905SS-6B">6b</A> Mondal M. Argade NP. Tetrahedron Lett. 2004, 45: 5693 <A NAME="RZ04905SS-6C">6c</A> Mondal M. Argade NP. Synlett 2004, 1243 <A NAME="RZ04905SS-6D">6d</A> Mangaleswaran S. Argade NP. Synthesis 2004, 1560 <A NAME="RZ04905SS-6E">6e</A> Mhaske SB. Argade NP. Tetrahedron 2004, 60: 3417 <A NAME="RZ04905SS-6F">6f</A> Argade NP. Balasubramaniyan V. Heterocycles 2000, 53: 475 ; and references cited therein <A NAME="RZ04905SS-7">7</A> Rondestvedt CS. Vogl O. J. Am. Chem. Soc. 1955, 77: 2313