Synlett, Table of Contents LETTER © Georg Thieme Verlag Stuttgart · New York An Enantiospecific Approach to 8,9-seco-C-Aromatic Taxanes A. Srikrishna*, P. Ravi Kumar, V. PadmavathiDepartment of Organic Chemistry, Indian Institute of Science, Bangalore 560 012, India.Fax: +91(80)3600683; e-Mail: ask@orgchem.iisc.ernet.in); Recommend Article Abstract Buy Article All articles of this category Abstract An enantiospecific approach to functionalised C-aromatic-8,9-seco-taxanes starting from the readily available monoterpene (R)-carvone is described. Key words C-aromatic-8,9-seco-taxanes - Paclitaxel - antitumor activity - carvone Full Text References References1 INSA Visiting Scientist. Present address: Department of Chemistry, Sri Venkateswara University, Tirupathi 517502, India. 2 Wani MC. Taylor HL. Wall ME. Coggon P. McPhail AT. J. Am. Chem. Soc. 1971, 93: 2325 For reviews, see: 3a Swindell CS. Org. Prep. Proced. Int. 1991, 23: 465 3b Tetrahedron Symposia in Print: Tetrahedron Winkler JD. Elsevier; Amsterdam: 1992. p.6953 3c Kingston DGI. Molinero AA. Rimoldi JM. Progress in the Chemistry of Organic Natural Products Springer-Verlag; New York: 1993. p.61 3d Guenard D. Gueritte-Voegelein F. Potier P. Acc. Chem. Res. 1993, 26: 160 3e Boa AN. Jenkins PR. Lawrence NJ. Contemp. Org. Synth. 1994, 1: 47 3f Nicolaou KC. Dai WM. Guy RK. Angew. Chem., Int. Ed. Engl. 1994, 33: 15 3g Taxane Anticancer Agents: Basic Science and Current Status Georg GI. Chen TT. Ojima I. Vyas DM. ACS Symposium Series 583, American Chemical Society; Washington, DC: 1995. 3h Taxol Science and Applications Suffness M. CRC; Boca Raton: 1995. 3i Wender PA. Natchus MG. Shuker AJ. In Taxol® Science and Applications Suffness M. CRC Press; New York: 1995. p.123 3j Mehta G. Singh V. Chem. Rev. 1999, 99: 881 4 For the total synthesis of taxol, and the recent approaches to taxanes, see: Uttaro J.-P. Audran G. Galano J.-M. Monti H. Tetrahedron Lett. 2002, 43: 2757 ; and references cited therein 5a Srikrishna A. Reddy TJ. Kumar PP. Chem. Commun. 1996, 1369 5b Srikrishna A. Reddy TJ. Kumar PP. J. Chem. Soc., Perkin Trans. 1 1998, 3143 5c For the synthesis of antipodal A-ring of taxanes from (R)-carvone, see: Mehta G. Chattopadhyay SK. Umarye JD. Tetrahedron Lett. 1999, 40: 4881 6 Buchi G. Egger B. J. Org. Chem. 1971, 36: 2021 7 Schreiber SL. Liew W.-F. Tetrahedron Lett. 1983, 24: 2363 8 Srikrishna A. Anebouselvy K. Reddy TJ. Tetrahedron Lett. 2000, 41: 6643 9a Srikrishna A. Reddy TJ. Indian J. Chem., Sect. B 1995, 34: 844 9b Srikrishna A. Reddy TJ. Arkivoc 2001, 9 10 Garver L. van Eikeren P. Byrd JE. J. Org. Chem. 1976, 41: 2773
