Stereoselective Total Synthesis of iso-Cladospolide B

Abstract

A simple and efficient stereoselective total synthesis of iso-cladospolide B and a formal total synthesis of cladospolide B, using Jacobsen’s hydrolytic kinetic resolution, is described.

Key words

phytotoxic - Wadsworth-Emmons - oxidation - kinetic resolution - Mitsunobu

References

• 1 Biabani MAF. Laatsch H. J. Prakt. Chem.  1998,  340:  589 
• 2a Cameron JS. Abbanat D. Bernan VS. Maiese WM. Greenstein M. Jompa J. Tahir A. Ireland CM. J. Nat. Prod.  2000,  63:  142 
• 2b Brauers G. Edrada RA. Ebel R. Proksch P. Wray V. Berg A. Grage U. Schachtele C. Totzke F. Finkezneller G. Marme D. Kraus J. Munchbach M. Michel M. Bringmann G. Schaumann K. J. Nat. Prod.  2000,  63:  739 
• 2c Gestner S. Cohen N. Ilan M. Yarden O. Carmeli S. J. Nat. Prod.  2005,  68:  1350 
• 3 Fuji Y. Fukuda A. Hamasaki T. Ichimoto I. Nakajima H. Phytochemistry  1995,  40:  1443 
• 4a Pandey SK. Kumar P. Tetrahedron Lett.  2005,  46:  6625 
• 4b Franck X. Vaz Araujo ME. Jullian JC. Hocquemiller R. Figadere B. Tetrahedron Lett.  2001,  42:  2801 
• 4c Austin KAB. Banwell MG. Loong DTJ. Rae D. Willis AC. Org. Biomol. Chem.  2005,  3:  1081 
• 5a Yadav JS. Vishweshwar RK. Sridhar RM. Prasad AR. Tetrahedron Lett.  2006,  47:  4393 
• 5b Yadav JS. Prathap I. Padmaja TB. Tetrahedron Lett.  2006,  47:  3773 
• 5c Yadav JS. Krishnam Raju A. Purushotham RP. Rajaiah G. Tetrahedron: Asymmetry  2005,  16:  3283 
• 5d Sabitha G. Swapna R. Satheesh BR. Yadav JS. Tetrahedron Lett.  2005,  46:  6145 
• 5e Yadav JS. Sridhar Reddy M. Prasad AR. Tetrahedron Lett.  2005,  46:  2133 
• 5f Sabitha G. Rajkumar M. Shashi Kumar RM. Yadav JS. Ramakrishna KVS. Kunwar AC. Tetrahedron Lett.  2005,  46:  1659 
• 5g Sudhakar K. Sabitha G. Mallikarjuna RN. Rajkumar M. Yadav JS. Tetrahedron Lett.  2005,  46:  6567 
• 5h Yadav JS. Bhaskar RK. Sabitha G. Tetrahedron Lett.  2004,  45, 6475 
• 5i Yadav JS. Srihari P. Tetrahedron: Asymmetry  2004,  15:  81 
• 6a Tokunaga M. Larrow JF. Kakiuchim F. Jacobsen EN. Science  1997,  277:  936 
• 6b For earlier publications using Salen complexes from our group, see ref. 5i and: Yadav JS. Bandyopadhyay A. Kunwar AC. Tetrahedron Lett.  2001,  43:  4907 
• 7 Mitsunobu O. Synthesis  1981,  1 
• 8a Julia M. Paris JM. Tetrahedron Lett.  1973,  14:  4833 
• 8b

  Other bases were employed without success.

• 9 Garegg J. Samuelsson B. J. Chem. Soc., Perkin Trans. 1  1980,  2866 
• 10a Hungebuhler E. Seebach D. Helv. Chim. Acta.  1981,  64:  687 
• 10b Mukayama T. Suzuki K. Yamada T. Chem. Lett.  1982,  929 
• 12 Inanaga J. Hirata K. Sacki H. Katsuki T. Yamaguchi M. Bull. Chem. Soc. Jpn.  1979,  52:  1989 

11

The physical and spectroscopic data were in full agreement with the literature (ref. 4b).