Synlett, Table of Contents LETTER© Georg Thieme Verlag Stuttgart · New YorkAn Enantiospecific Approach to 8,9-seco-C-Aromatic TaxanesA. 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(opens in new window) All articles of this category(opens in new window) 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 References<A NAME="RD17302ST-1">1</A> INSA Visiting Scientist. Present address: Department of Chemistry, Sri Venkateswara University, Tirupathi 517502, India. <A NAME="RD17302ST-2">2</A> Wani MC. Taylor HL. Wall ME. Coggon P. McPhail AT. J. Am. Chem. Soc. 1971, 93: 2325 For reviews, see: <A NAME="RD17302ST-3A">3a</A> Swindell CS. Org. Prep. Proced. Int. 1991, 23: 465 <A NAME="RD17302ST-3B">3b</A> Tetrahedron Symposia in Print: Tetrahedron Winkler JD. Elsevier; Amsterdam: 1992. p.6953 <A NAME="RD17302ST-3C">3c</A> Kingston DGI. Molinero AA. Rimoldi JM. Progress in the Chemistry of Organic Natural Products Springer-Verlag; New York: 1993. p.61 <A NAME="RD17302ST-3D">3d</A> Guenard D. Gueritte-Voegelein F. Potier P. Acc. Chem. Res. 1993, 26: 160 <A NAME="RD17302ST-3E">3e</A> Boa AN. Jenkins PR. Lawrence NJ. Contemp. Org. Synth. 1994, 1: 47 <A NAME="RD17302ST-3F">3f</A> Nicolaou KC. Dai WM. Guy RK. Angew. Chem., Int. Ed. Engl. 1994, 33: 15 <A NAME="RD17302ST-3G">3g</A> 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. <A NAME="RD17302ST-3H">3h</A> Taxol Science and Applications Suffness M. CRC; Boca Raton: 1995. <A NAME="RD17302ST-3I">3i</A> Wender PA. Natchus MG. Shuker AJ. In Taxol® Science and Applications Suffness M. CRC Press; New York: 1995. p.123 <A NAME="RD17302ST-3J">3j</A> Mehta G. Singh V. Chem. Rev. 1999, 99: 881 <A NAME="RD17302ST-4">4</A> 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 <A NAME="RD17302ST-5A">5a</A> Srikrishna A. Reddy TJ. Kumar PP. Chem. Commun. 1996, 1369 <A NAME="RD17302ST-5B">5b</A> Srikrishna A. Reddy TJ. Kumar PP. J. Chem. Soc., Perkin Trans. 1 1998, 3143 <A NAME="RD17302ST-5C">5c</A> For the synthesis of antipodal A-ring of taxanes from (R)-carvone, see: Mehta G. Chattopadhyay SK. Umarye JD. Tetrahedron Lett. 1999, 40: 4881 <A NAME="RD17302ST-6">6</A> Buchi G. Egger B. J. Org. Chem. 1971, 36: 2021 <A NAME="RD17302ST-7">7</A> Schreiber SL. Liew W.-F. Tetrahedron Lett. 1983, 24: 2363 <A NAME="RD17302ST-8">8</A> Srikrishna A. Anebouselvy K. Reddy TJ. Tetrahedron Lett. 2000, 41: 6643 <A NAME="RD17302ST-9A">9a</A> Srikrishna A. Reddy TJ. Indian J. Chem., Sect. B 1995, 34: 844 <A NAME="RD17302ST-9B">9b</A> Srikrishna A. Reddy TJ. Arkivoc 2001, 9 <A NAME="RD17302ST-10">10</A> Garver L. van Eikeren P. Byrd JE. J. Org. Chem. 1976, 41: 2773