Synthesis, Table of Contents PAPER © Georg Thieme Verlag Stuttgart · New York A Facile Synthesis of the Angucyclinone Antibiotic (+)-Rubiginone B2 Involving the BF3-Mediated Diels-Alder Reaction of Juglone Jiro Motoyoshiya*, Yusuke Masue, Gento Iwayama, Sachiko Yoshioka, Yoshinori Nishii, Hiromu AoyamaDepartment of Chemistry, Faculty of Textile Science and Technology, Shinshu University, Ueda, Nagano, 386-8567 JapanFax: +81(268)215391; e-Mail: jmotoyo@giptc.shinshu-u.ac.jp; Recommend Article Abstract Buy Article All articles of this category Abstract A short synthesis of (+)-rubiginone B2 is reported. The BF3-mediated Diels-Alder reaction of juglone and (R)-3-methyl-1-vinylcyclohexene followed by aromatization gave the anthraquinone as the desired regioisomer, which was converted into the target antibiotic after a two-step operation. Key words angucyclinone antibiotics - asymmetric synthesis - quinines - Diels-Alder reactions - photooxidations Full Text References References 1 Thomson RH. In Naturally Occurring Quinones III Chapman and Hall; London: 1987. Chap. 6. 2 Oka M. Kamei H. Hamagishi Y. Tomita K. Miyaki T. Konishi M. Oki T. J. Antibiotics 1990, 43: 967 3 Bowie JH. Johnson AW. Tetrahedron Lett. 1967, 1449 4a Brown PM. Thomson RH. J. Chem. Soc., Perkin Trans. 1 1976, 997 4b Uemura M. Take K. Minami T. Hayashi Y. Tetrahedron 1985, 41: 5771 4c Katsuura K. Snieckus V. Can. J. Chem. 1987, 65: 124 4d Guingant A. Barreto M. Tetrahedron Lett. 1987, 28: 3107 4e Kraus GA. Wu Y. Tetrahedron 1987, 28: 3107 4f Kraus GA. Wu Y. Tetrahedron 1987, 28: 3107 4g Kraus GA. Wu Y. Tetrahedron Lett. 1991, 32: 3803 4h Krohn K. Khanbabaee K. Jones PG. Chrapowski A. Liebigs Ann. Chem. 1994, 1109 4i Krohn K. Khanbabaee K. Liebigs Ann. Chem. 1994, 1109 4j Krohn K. Boeker N. Floerke U. Freund C. J. Org. Chem. 1997, 62: 2350 4k Patil ML. Borate HB. Ponde DE. Bhawal BM. Deshpande VH. Tetrahedron Lett. 1999, 40: 4437 4l Mal D. Roy HN. J. Chem. Soc., Perkin Trans. 1 1999, 3167 4m Krohn K. Mcheel J. Zukowski M. Tetrahedron 2000, 56: 4753 4n Rozek T. Bowie JH. Pyke SM. Skelton BW. White AH. J. Chem. Soc., Perkin Trans. 1 2001, 1826 5a Boyd VA. Sulikowski GA. J. Am. Chem. Soc. 1995, 117: 8472 5b Larsen DS. O’Shea MD. Brooker S. Chem. Commun. 1996, 203 5c Carreno MC. Urbano A. Vitta CD. Chem. Commun. 1999, 817 5d Caygill GB. Larsen DS. Brooker S. J. Org. Chem. 2001, 66: 7427 5e Carreno MC. Ribagorda M. Somoza A. Urbano A. Angew. Chem. Int. Ed. 2002, 41: 2755 5f Kalogerakis A. Groth U. Synlett 2003, 1886 6 Ohgaki E. Motoyoshiya J. Narita S. Kakurai T. Hayashi S. Hirakawa K. J. Chem. Soc., Perkin Trans. 1 1990, 3109 7 Motoyoshiya J. Kameda T. Asari M. Miyamoto M. Narita S. Aoyama H. Hayashi S. J. Chem. Soc., Perkin Trans. 2 1997, 1845 8a Alston PV. Ottenbrite RM. J. Org. Chem. 1975, 40: 1111 8b Alston PV. Gordon MD. Ottenbrite RM. Cohen T. J. Org. Chem. 1983, 48: 5051 8c Gunter OF. Ottenbrite RM. Shillady DD. Alston PV. J. Org. Chem. 1987, 52: 391 9 Krohn K. Ballwanz F. Baltus W. Liebigs Ann. Chem. 1993, 911 10 Merril JR. Bennet RG. J. Chem. Phys. 1965, 43: 1410
