Synthesis, Table of Contents PAPER © Georg Thieme Verlag Stuttgart · New York Stereoselective Total Synthesis of (+)-Virol C Gowravaram Sabitha*, Ch. Srinivas Reddy, Pabbaraja Srihari, Jhillu Singh YadavOrganic Division - I, Indian Institute of Chemical Technology, Hyderabad, IndiaFax: +91(402)716012; e-Mail: sabitha@iict.ap.nic.in; Recommend Article Abstract Buy Article All articles of this category Abstract A highly stereoselective synthesis of (+)-Virol C (1) has been achieved starting from octan-1-ol (6) using two different strategies, elimination reactions of epoxyallyl chloride 12 and epoxy chloride 16 to hydroxyenyne 2 and trans-hydroxyalkenyl chloride 4 as key reactions in route a and route b, respectively. Key words Virol C - stereoselective - elimination reaction - Cadiot-Chodkiewicz coupling - Sonogashira Full Text References References 1 Jacobson A. J. Am. Chem. Soc. 1915, 37: 916 2a Anet EFLJ. Silk MH. Trippett S. Chem. Ind. (London) 1952, 757 2b Anet EFLJ. Silk MH. Trippett S. J. Chem. Soc. 1953, 309 3a Wittstock U. Lichtnow KH. Teuscher E. Planta Med. 1997, 63: 120 3b Konoshima T. Lee KH. J. Nat. Prod. 1986, 49: 1117 4a Uwai K. Oshima Y. Sugihara T. Ohta T. Tetrahedron 1999, 55: 9469 4b Ohta T. Uwai K. Kuchi R. Nozoe S. Oshima Y. Sasaki K. Yoshizaki R. Tetrahedron 1999, 55: 12087 5 Stefani HA. Menezer PH. Costa IM. Silva DO. Petragnani N. Synlett 2002, 1335 6a Katsuki T. Sharpless KB. J. Am. Chem. Soc. 1980, 102: 5974 6b Rossiter BE. Katsuki T. Sharpless KB. J. Am. Chem. Soc. 1982, 103: 464 7 Yadav JS. Barma DK. Dutta D. Tetrahedron Lett. 1997, 38: 4479 8 Hofmeister H. Laurent HK. Wiechert R. Angew. Chem., Int. Ed. Engl. 1984, 23: 727 9 Brandsma L. Preparative Acetylene Chemistry 2nd ed.: Elsevier; Amsterdam: 1988. Chap. 10. p.212 10 Chemin D. Linstrumelle G. Tetrahedron 1994, 50: 5335 11a Sonogashira K. Tohda Y. Hagihara N. Tetrahedron Lett. 1975, 4467 11b Alami M. Linstrumelle G. Tetrahedron Lett. 1991, 32: 6109 11c Alami M. Crousse B. Linstrumelle G. Tetrahedron Lett. 1994, 35: 3543
