DOI: 10.1039/A704596D
(Paper)
Reference Section for: Chem. Commun., 1997, 1787-1788
The efficient and regioselective synthesis of the naphthoquinone core of streptovaricin U
(Note: The full text of this document is currently only available in the PDF Version )
Masaaki Miyashita, Takahiro Yamasaki, Tomonori Shiratani, Susumi Hatakeyama, Masahiro Miyazawa and Hiroshi Irie
Abstract
The efficient and regioselective synthesis of the naphthoquinone core of streptovaricin U 1 via the Diels–Alder reaction of 1-methoxy-2-methyl-3-trimethylsilyloxybuta-1,3-diene 5 with the 2,6-dibromo-3-methyl-1,4-benzoquinone 6 is described.
References
- K. L. Reinhart, Jr. and L. S. Shield, Fortschr. Chem. Org. Naturst., 1976, 33, 231 Search PubMed; P. V. Desshmukh, K. Kakinuma, J. J. Ameel, K. L. Reinhart, Jr., P. F. Wiley and L. H. Li, J. Am. Chem. Soc., 1976, 98, 870 CrossRef; K. L. Reinhart, Jr., F. J. Antosz, P. V. Desshmukh, K. Kakinuma, P. K. Martin, B. I. Milavetz, K. Sasaki, T. R. Willy, L. H. Li and F. Reusser, Antibiotics, 1976, 29, 201 Search PubMed.
- P. A. McCarthy, Tetrahedron Lett., 1982, 23, 4199 CrossRef CAS; B. M. Trost and W. H. Pearson, Tetrahedron Lett., 1983, 24, 269 CrossRef CAS; B. Fraser-Reid, L. Magdzinski, B. F. Molino and D. R. Mootoo, J. Org. Chem., 1987, 52, 4495 CrossRef CAS; B. Fraser-Reid, B. F. Molino, L. Magdzinski and D. R. Mootoo, ibid., 1987, 52, 4505 Search PubMed; D. R. Mootoo and B. Fraser-Reid, ibid., 1987, 52, 4511 Search PubMed; P. A. McCarthy and M. Kageyama, ibid., 1987, 52, 4681 Search PubMed; W. R. Roush and A. D. Palkowitz, ibid., 1989, 54, 3009 Search PubMed; D. R. Mootoo and B. Fraser-Reid, ibid., 1989, 54, 5548 Search PubMed; Z. Wang and S. L. Schreiber, Tetrahedron Lett., 1990, 31, 31 CrossRef CAS; D. R. Mootoo and B. Fraser-Reid, J. Chem. Soc., Perkin Trans. 1, 1990, 739 RSC; Tetrahedron, 1990, 46, 185 Search PubMed; W. R. Roush and D. J. Madar, Tetrahedron Lett., 1993, 34, 1553 Search PubMed.
- M. Miyashita, T. Shiratani, K. Kawamine, S. Hatakeyama and H. Irie, Chem. Commun., 1996, 1027 RSC.
- M. Miyashita, M. Hoshino and A. Yoshikoshi, J. Org. Chem., 1991, 56, 6483 CrossRef CAS.
- W. M. J. Knoll, K. L. Rinehart, Jr., P. F. Wiley and L. H. Li, J. Antibiot., 1980, 33, 249 CAS.
- S. Danishefsky, C.-F. Yan, R. K. Singh, R. B. Gammill, P. M. McCurry, Jr., N. Fritsch and J. Clardy, J. Am. Chem. Soc., 1979, 101, 7001 CrossRef CAS; A. P. Kozikowski and K. Sugiyama, Tetrahedron Lett., 1980, 21, 3257 CrossRef CAS.
- S. Sugasawa, S. I. Yamada and M. Harahashi, J. Pharm. Soc. Jpn., 1951, 71, 1345 Search PubMed.
- B. M. Trost and W. H. Pearson, Tetrahedron Lett., 1983, 24, 269 CrossRef CAS.