Stereoconvergent Transformation of 1,2a-Disubstituted Benzo[b]cyclo­buta[d]pyrans to 1,3-Disubstituted Tetrahydrodibenzofuran-4-ols and its ­Application to the Second-Generation Synthesis of (±)-Linderol A

Abstract

1,2a-Disubstituted benzo[b]cyclobuta[d]pyrans, which were prepared by photochemical [2+2] cycloaddition between coumarins and alkenes, were treated with two equivalents of dimethylsulfoxonium methylide. 1,3-Disubstituted tetrahydrodibenzofurans having r-1,t-4a,t-9b stereochemistry were obtained stereoconvergently regardless of the stereochemistry of the 1-position in the cyclobutane derivatives. This methodology was applied to the second-generation synthesis of (±)-linderol A, a melanin biosynthesis inhibitory active natural product.

Key words

stereoconvergent reaction - ylides - photochemistry - Linderol A - fused-ring systems

References

• Recent reviews:
• 1a Taylor RE. Engelhardt FC. Schmitt MJ. Tetrahedron  2003,  59:  5623 
• 1b Pietruszka J. Chem. Rev.  2003,  103:  1051 
• 1c Wessjohann LA. Brandt W. Thiemann T. Chem. Rev.  2003,  103:  1625 
• 1d Donaldson WA. Tetrahedron  2001,  57:  8589 
• 1e Hansen TV. Stenstrom Y. Org. Synth.: Theory Appl.  2001,  5:  1 
• Recent reviews:
• 2a Dolbier WR. Battiste MA. Chem. Rev.  2003,  103:  1071 
• 2b Fedory ski M. Chem. Rev.  2003,  103:  1099 
• 2c Sydnes LK. Chem. Rev.  2003,  103:  1133 
• 2d Reissig H.-U. Zimmer R. Chem. Rev.  2003,  103:  1151 
• 2e Baldwin JE. Chem. Rev.  2003,  103:  1197 
• 2f Brandi A. Cicchi S. Cordero FM. Goti A. Chem. Rev.  2003,  103:  1213 
• 2g Baird M. Chem. Rev.  2003,  103:  1271 
• 2h Nakamura M. Isobe H. Nakamura E. Chem. Rev.  2003,  103:  1295 
• 2i Lee-Ruff E. Mladenova G. Chem. Rev.  2003,  103:  1449 
• 2j Namyslo JC. Kaufmann DE. Chem. Rev.  2003,  103:  1485 
• 2k Donaldson WA. Tetrahedron  2001,  57:  8589 
• 2l Sydnes LK. Eur. J. Org. Chem.  2000,  3511 
• 2m Iwasawa N. Narasaka K. Top. Curr. Chem.  2000,  207:  69 
• 2n de Meijere A. Kozhushkov SI. Khlebnikov AF. Top. Curr. Chem.  2000,  207:  89 
• 2o de Meijere A. Kozhushkov SI. Hadjiarapoglou LP. Top. Curr. Chem.  2000,  207:  149 
• 2p Nemoto H. Fukumoto K. Synlett  1997,  863 
• 2q Brandi A. Cordero FM. De Sarlo F. Goti A. Guarna A. Synlett  1993,  1 
• 3a Yamashita M. Okuyama K. Kawajiri T. Takada A. Inagaki Y. Nakano H. Tomiyama M. Ohnaka A. Terayama I. Kawasaki I. Ohta S. Tetrahedron  2002,  58:  1497 
• 3b Yamashita M. Okuyama K. Ohhara T. Kawasaki I. Michihiro Y. Sakamaki K. Ito S. Ohta S. Chem. Pharm. Bull.  1999,  47:  1439 
• 3c Yamashita M. Okuyama K. Ohhara T. Kawasaki I. Ohta S. Synlett  1996,  547 
• 3d Yamashita M. Okuyama K. Ohhara T. Kawasaki I. Sakai K. Nakata S. Kawabe T. Kusumoto M. Ohta S. Chem. Pharm. Bull   1995.  43:  p.2075 
• 3e Yamashita M. Okuyama K. Kawasaki I. Ohta S. Tetrahedron Lett.  1995,  36:  5603 
• 3f Yamashita M. Okuyama K. Ohhara T. Kawasaki I. Ohta S. Chem. Pharm. Bull.  1995,  43:  708 
• 4 Mimaki Y. Kameyama A. Sashida Y. Miyata Y. Fujii A. Chem. Pharm. Bull.  1995,  43:  893 
• 5a Schwebel D. Margaretha P. Helv. Chim. Acta   2000,  83:  1168 
• 5b Schwebel D. Ziegenbalg J. Kopf J. Margatetha P. Helv. Chim. Acta  1999,  82:  177 
• 5c Ratiner BD. Lisa LP. Otsuki T. Chem. Express  1990,  5:  225 
• 5d Ratiner BD. Otsuki T. Chem. Lett.  1989,  1035 
• 5e Pfoertner K.-H. Helv. Chim. Acta  1976,  59:  834 
• 6a Corey EJ. Chaykovsky M. J. Am. Chem. Soc.  1965,  87:  1353 
• 6b Gololobov YG. Nesmeyanov AN. Lysenko VP. Boldeskul IE. Tetrahedron  1987,  43:  2609 
• 6c Ng JS. Liu C. In Encyclopedia of Reagents for Organic Synthesis   Vol. 3:  Paquette LA. John Wiley and Sons; Chichester: 1995.  p.2159 
• 7a Yamashita M. Ohta N. Shimizu T. Matsumoto K. Matsuura Y. Kawasaki I. Tanaka T. Maezaki N. Ohta S. J. Org. Chem.  2003,  68:  1216 
• 7b Yamashita M. Ohta N. Kawasaki I. Ohta S. Org. Lett.  2001,  3:  1359