Synlett, Table of Contents LETTER © Georg Thieme Verlag Stuttgart · New York 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 Masayuki Yamashita, Tomoki Inaba, Takashi Shimizu, Ikuo Kawasaki, Shunsaku Ohta*Kyoto Pharmaceutical University, Misasagi-Nakauchicho 5, Yamashinaku, Kyoto 607-8414, JapanFax: +81(75)5954795; e-Mail: sohta@mb.kyoto-phu.ac.jp; Recommend Article Abstract Buy Article All articles of this category 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 Full Text References 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 Fedoryski 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
