Intramolecular [3+4] allyl cation cycloaddition: Novel route to hydroazulenes
作者： Raymond J. Giguere , Scott M. Duncan , Joseph M. Bean , Leslie Purvis
DOI: 10.1016/S0040-4039(00)82267-4
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摘要: Abstract Intramolecular Hoffmann-Noyori reaction of acyclic trienol 6 permits direct entry to hydoazulenes 7a, b with modest diastereoselectivity. Cycloaddition precursor is readily prepared from 1,5-pentanediol in seven steps.
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sci-hub.se 参考文章(30)
James H. Rigby, Jo Ann Zbur Wilson, A general approach to the synthesis of C8-oxygenated guaianolides Journal of Organic Chemistry. ,vol. 52, pp. 34- 44 ,(1987) , 10.1021/JO00377A006
Alan P. Kozikowski, Benjamin B. Mugrage, B.C. Wang, Zhang-bao Xu, The INOC approach to the hydroazulenone ring system - a potential entry tot he guaianolides and pseudoguaianolides. Tetrahedron Letters. ,vol. 24, pp. 3705- 3708 ,(1983) , 10.1016/S0040-4039(00)94514-3
Tomas Hudlicky, Serengulam V. Govindan, James O. Frazier, Heteroatom cyclopentene annulation. Synthesis of guaiane ring system Journal of Organic Chemistry. ,vol. 50, pp. 4166- 4171 ,(1985) , 10.1021/JO00221A043
Junzo Ukai, Yoshihiko Ikeda, Nobuo Ikeda, Hisashi Yamamoto, Direct, stereoselective synthesis of either E- or Z-1,3-dienes Tetrahedron Letters. ,vol. 24, pp. 4029- 4032 ,(1983) , 10.1016/S0040-4039(00)88254-4
H. M. R. Hoffmann, Syntheses of Seven‐ and Five‐Membered Rings from Allyl Cations Angewandte Chemie. ,vol. 12, pp. 819- 835 ,(1973) , 10.1002/ANIE.197308191
Herbert O. House, Glenn S. Nomura, Don VanDerveer, Jane E. Wissinger, Perhydroazulenes. 6. 4-Keto derivatives with bridgehead methyl substituents Journal of Organic Chemistry. ,vol. 51, pp. 2408- 2416 ,(1986) , 10.1021/JO00363A002
James H. Rigby, Chrisantha Senanayake, Total synthesis of (.+-.)-grosshemin Journal of the American Chemical Society. ,vol. 109, pp. 3147- 3149 ,(1987) , 10.1021/JA00244A049
James H. Rigby, JoAnn Zbur Wilson, Total synthesis of guaianolides: (.+-.)-dehydrocostus lactone and (.+-.)-estafiatin Journal of the American Chemical Society. ,vol. 106, pp. 8217- 8224 ,(1984) , 10.1021/JA00338A035
Herbert O. House, Glenn S. Nomura, Don VanDerveer, Perhydroazulenes. 7. Effect of a tert-butyl substituent at carbon-6 upon the properties of the 4-keto derivatives Journal of Organic Chemistry. ,vol. 51, pp. 2416- 2423 ,(1986) , 10.1021/JO00363A003
Michael Sworin, Ko Chung Lin, Cyclopentanoid synthesis via the intramolecular trapping of oxy cope intermediates stereocontrolled synthesis of the cis and trans hydroazulene skeleton Journal of Organic Chemistry. ,vol. 52, pp. 5640- 5642 ,(1987) , 10.1021/JO00234A029