Influence of alkene substituent in dictating the reaction course to form carbocycles or oxacycles during ring closing metathesis of acyclic trienes
Author:
Funder
SERB J. C. Bose National Fellowship
Indian National Science Academy
Publisher
Springer Science and Business Media LLC
Subject
General Chemistry
Link
http://link.springer.com/article/10.1007/s12039-017-1390-3/fulltext.html
Reference9 articles.
1. For excellent accounts on RCM see: (a) Grubbs R H, Miller S J and Fu G C 1995 Ring-Closing Metathesis and Related Processes in Organic Synthesis Acc. Chem. Res. 28 446; (b) Fürstner A 1997 Recent advancements in Ring Closing Olefin Metathesis Top. Catal. 4 285; (c) Schuster M and Blechert S 1997 Olefin Metathesis in Organic Chemistry Angew. Chem. Int. Ed. 36 2036; (d) Grubbs R H and Chang S 1998 Recent Advances in Olefin Metathesis and Its Application in Organic Synthesis Tetrahedron 54 4413; (e) Armstrong S K 1998 Ring Closing Diene Metathesis in Organic Synthesis J. Chem. Soc. Perkin Trans. 1 371; (f) Fürstner A 2000 Olefin Metathesis and Beyond Angew. Chem. Int. Ed. 39 3012; (g) Kotha S and Sreenivasachary N 2001 Catalytic Metathesis Reaction in Organic Synthesis Indian J. Chem. B40 763; (h) Deiters A and Martin S F 2004 Synthesis of Oxygen- and Nitrogen-Containing Heterocycles by Ring-Closing Metathesis Chem. Rev. 104 2199; (i) Nicolaou K C, Bulger P G and Sarlah D 2005 Metathesis Reactions in Total Synthesis Angew. Chem. Int. Ed. 44 4490; (j) Ghosh S, Ghosh S and Sarkar N 2006 Factors Influencing Ring Closure Through Olefin Metathesis-A Perspective J. Chem. Sci. 118 223; (k) Chattopadhyay S K, Karmakar S, Biswas T, Majumdar K C, Rahaman H and Roy B 2007 Formation of Medium-Ring Heterocycles by Diene and Enyne Metathesis Tetrahedron 63 3919
2. Ghosh S, Ghosh S and Sarkar N 2006 Factors Influencing Ring Closure Through Olefin Metathesis-A Perspective J. Chem. Sci. 118 223
3. (a) Maity S, Matcha K and Ghosh S 2010 Synthetic Studies on Schisandra Nortriterpenoids. Stereocontrolled Synthesis of Enantiopure C-5-epi ABC Ring Systems of Micrandilactone A and Lancifodilactone G Using RCM J. Org. Chem. 75 4192; (b) Mondal S, Yadav R N and Ghosh S 2011 Influence of Diene Substituent Position on the Stereochemical Outcome in IMDA Reaction of Decatrienones. An Asymmetric Synthesis of $$\text{C}_{10}$$ C 10 -epi-Dihydro-epi-deoxy Arteannuin B Org. Lett. 13 6078; (c) Bose S, Ghosh M and Ghosh S 2012 Domino Ring-Opening Metathesis-Ring-Closing Metathesis of Bicyclo[2.2.2]octene Derivatives: Scope and Limitations J. Org. Chem. 77 6345; (d) Datta R and Ghosh S 2017 Total Synthesis of the Marine Polyketide (-)-Gracilioether F J. Org. Chem. 82 7675
4. (a) Festa C, Lauro G, Marino S D, D’Auria M V, Monti M C, Casapullo A, D’Amore C, Renga, B, Mencarelli A, Petek S, Bifulco G, Fiorucci S and Zampella A 2012 Plakilactones from the Marine Sponge Plakinastrella mamillaris. Discovery of a New Class of Marine Ligands of Peroxisome Proliferator-Activated Receptor $$\gamma $$ γ J. Med. Chem. 55 8303; (b) Norris M D and Perkins M V 2016 Total Synthesis of Plakilactones C, B and des-Hydroxyplakilactone B by the Oxidative Cleavage of Gracilioether Furanylidenes J. Org. Chem. 81 6848
5. (a) Baylon C, Heck M-P and Mioskowski C 1999 Bis Ring Closing Olefin Metathesis for the Synthesis of Unsaturated Polycyclic Ethers. O-Membered Ring Cyclization in Favor of C-Membered Ring Cyclization J. Org. Chem. 64 3354; (b) Heck M-P, Baylon C, Nolan S P and Mioskowski C 2001 Triple Ring Closing Metathesis Reaction: synthesis of Adjacent Cyclic Ethers Org. Lett. 3 1989
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