Synthesis, Table of Contents Synthesis 2015; 47(19): 2997-3008DOI: 10.1055/s-0034-1380864 paper © Georg Thieme Verlag Stuttgart · New York Stereoselective Total Synthesis of (+)-Anamarine and 8-epi-(–)-Anamarine from d-Mannitol Rajender Karnekanti* a Organic and Biomolecular Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India b Govt. Model Residential Polytechnic, Bhadrachalam, Telangana 507 111, India Email: rajenderpoly@gmail.com , Marumamula Hanumaiah a Organic and Biomolecular Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India , Gangavaram V. M. Sharma a Organic and Biomolecular Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India › Author Affiliations Recommend Article Abstract Buy Article All articles of this category Abstract Stereoselective total synthesis of (+)-anamarine and the first synthesis of 8-epi-(–)-anamarine, its nonnatural diastereomer, were achieved from readily available d-mannitol. The key reactions involved were asymmetric dihydroxylation, cross-metathesis and ring-closing metathesis reactions. The approach is adoptable advantageously for the diversity-oriented synthesis of several related classes of natural products. Key words Key words(+)-anamarine - 8-epi-(–)-anamarine - d-mannitol - asymmetric dihydroxylation - cross-metathesis and ring-closing metathesis Full Text References References 1 Marco JA, Carda M, Murga J, Falomir E. Tetrahedron 2007; 63: 2929 2 Kikuchi H, Sasaki K, Sekiya J, Maeda Y, Amagai A, Kubohara Y, Ohsima Y. Bioorg. Med. Chem. 2004; 12: 3203 3a Agrawal VK, Singh J, Mishra KC, Khadikar PV, Jaliwala YA. ARKIVOC 2006; (ii): 162 3b Hagen SE, Domagala JM, Gajda C, Lovdahl M, Tait BD, Wise E, Holler T, Hupe D, Nouhan C, Urumov A, Zeikus G, Zeikus E, Lunney EA, Pavlovsky A, Gracheck SJ, Saunders JM, VanderRoest S, Brodfuehrer J. J. Med. Chem. 2001; 44: 2319 3c Hagen SE, Vara-Prasad JV. N, Tait BD. Adv. Med. Chem. 2000; 5: 159 3d Aristoff PA. Drugs Future 1998; 23: 995 3e Romines KR, Chrusciel RA. Curr. Med. Chem. 1995; 2: 825 3f Chan KM, Rajab NF, Ishak MH. A, Ali AM, Yusoff K, Din LB, Inayat-Hussain SH. Chem.-Biol. Interact. 2006; 159: 129 3g Inayat-Hussain SH, Annuar BO, Din LB, Ali AM, Ross D. Toxicol. in Vitro 2003; 17: 433 3h Inayat-Hussain SH, Annuar BO, Din LB, Taniguchi N. Toxicol. Lett. 2002; 131: 153 3i Veena B, Sharma GV. M. Synlett 2014; 25: 1283 4 Marco JA, Carda M. Recent Advances in the Field of Naturally Occurring 5,6-Dihydropyran-2-ones. In Natural Lactones and Lactams, Synthesis, Occurrence and Biological Activity. Janecki T. Wiley-VCH; Weinheim: 2013: 51-100 5 Alemany A, Márquez C, Pascual C, Valverde S, Martínez-Ripoll M, Fayos J, Perales A. Tetrahedron Lett. 1979; 3583 6a Lorenz K, Lichtenthaler FW. Tetrahedron Lett. 1987; 28: 6437 6b Diaz-Oltra S, Murga J, Falomir E, Carda M, Marco JA. Tetrahedron 2004; 60: 2979 7 Gao D, Doherty GA. O. J. Org. Chem. 2005; 70: 9932 8 Sabitha G, Reddy CN, Gopal P, Yadav JS. Tetrahedron Lett. 2010; 51: 5736 9 Kumar KS, Reddy CS. Org. Biomol. Chem. 2012; 10: 2647 10a Prasad KR, Kumar SM. Tetrahedron 2014; 70: 4552 10b Reddy BV. S, Reddy VV, Praneeth K. Tetrahedron Lett. 2014; 55: 1398 11a Sharma GV. M, Mallesham S, Chandramouli C. Tetrahedron: Asymmetry 2009; 20: 2513 11b Mallesham S, Sharma GV. M. Tetrahedron: Asymmetry 2010; 21: 2646 11c Sharma GV. M, Chary DH, Chandramouli N, Achrainer F, Patrudu S, Zipse H. Org. Biomol. Chem. 2011; 9: 4079 11d Sharma GV. M, Sai Reddy P. Eur. J. Org. Chem. 2012; 2414 11e Sharma GV. M, Reddy SV, Ramakrishna KV. S. Org. Biomol. Chem. 2012; 10: 3689 11f Rajesh A, Sharma GV. M, Damera K. Tetrahedron Lett. 2014; 55: 4067 11g Rajesh A, Sharma GV. M, Damera K. Tetrahedron Lett. 2014; 55: 6474 11h Veena B, Sharma GV. M. Synlett 2014; 25: 2039 11i Sharma GV. M, Doddi VR. Macrolactones. In Natural Lactones and Lactams: Synthesis, Occurrence and Biological Activity. Janecki T. Wiley-VCH; Weinheim: 2013: 229-272 12a Chattopadhyay A, Mamdapur VR. J. Org. Chem. 1995; 60: 585 12b Chattopadhyay A. J. Org. Chem. 1996; 61: 6104 13a Mitsunobu O. Synthesis 1981; 1 13b Ahn C, Correia R, Deshong P. J. Org. Chem. 2002; 67: 1751 13c Swamy KC. K, Kumar NN. B, Balaraman E, Kumar KV. P. P. Chem. Rev. 2009; 109: 2551 14a Furstner A, Langemann K. J. Org. Chem. 1996; 61: 3942 14b Deiters A, Martin SF. Chem. Rev. 2004; 104: 2199 14c Vougioukalakis GC, Grubbs RH. Chem. Rev. 2010; 110: 1746 15 Saravanan P, Chandrasekhar M, Anand RV, Singh VK. Tetrahedron Lett. 1998; 39: 3091 16a Garegg PJ, Samuelsson B. Synthesis 1979; 813 16b Garegg PJ. Pure Appl. Chem. 1984; 56: 845 17 Ramesh P, Meshram HM. Tetrahedron Lett. 2012; 53: 4008 18 Yadav VK, Agrawal D. Chem. Commun. 2007; 5232 19 Martinelli MJ, Nayyar NK, Moher ED, Dhokte UP, Pawlak JM, Vaidyanathan P. Org. Lett. 1999; 1: 447 20 Alcaraz L, Harnett JJ, Mioskowski C, Martel JP, Le Gall T, Shin D.-S, Falck JR. Tetrahedron Lett. 1994; 35: 5449 21 Regeling H, Chitenden GJ. F. Carbohydr. Res. 1989; 190: 313 22 Xu D, Crispino GA, Sharpless KB. J. Am. Chem. Soc. 1992; 114: 7568 23a Schuster M, Blechert S. Angew. Chem., Int. Ed. Engl. 1997; 36: 2036 23b Armstrong SK. J. Chem. Soc., Perkin Trans. 1 1998; 371 23c Grubbs RH, Chang S. Tetrahedron 1998; 54: 4413 23d Trnka TM, Grubbs RH. Acc. Chem. Res. 2001; 34: 18 23e Nolen EG, Kurish AJ, Wong KA, Orlando MD. Tetrahedron Lett. 2003; 44: 2449 23f Grubbs RH. Tetrahedron 2004; 60: 7117 Supplementary Material Supplementary Material Supporting Information
