Total syntheses of PI-201 and related compounds

Bulletin of the Chemical Society of Japan

Volumn 69, Issue 12, 1996, Pages 3551-3561

  Murata, Takeshi ^a   Kumagai, Toshihito ^a   Ishikawa, Makoto ^a   Tadano, Kin Ichi ^a   Ogawa, Seiichiro ^a  

^a KEIO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1,2,4A,5,6,7,8,8A OCTAHYDRONAPHTHALENE DERIVATIVE; ANTICOAGULANT AGENT; NAPHTHALENE DERIVATIVE; PI 201; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030477088     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.69.3551     Document Type: Article

References (8)

1. Y. Kishimura, A. Kawashima, T. Kagamizono, M. Yamagishi, K. Matsumoto, Y. Kawashima, and K. Hanada, J. Antibiot., 45, 892 (1992).
2. 3 solution; personal communication from Dr. A. Kawashima (Taisho Pharmaceutical Co., Ltd.)
3. Total synthesis of 1 was reported in a preliminary communication form: K. Tadano, T. Murata, T. Kumagai, and S. Ogawa, Tetrahedron Lett., 34, 7279 (1993).
4. A relevant recent review on this subject, see: W. R. Roush, "Stereoselective and Synthetic Studies of the Intramolecular Diels-Alder Reaction," in "Advances in Cycloaddition," ed by D. P. Curran, JAI Press, Greenwich (1990), Vol. 2, p. 91.
5. 3), our sample was estimated to be more than 95% ee. See: K. Mori and H. Watanabe, Tetrahedron, 41, 3423 (1985).
6. K. Mori and H. Kishida, Tetrahedron, 42, 5281 (1986).
7. F. C. Chang and N. F. Wood, Tetrahedron Lett., 1964, 2969.
8. W. R. Roush, "Intramolecular Diels-Alder Reactions, " in "Comprehensive Organic Synthesis," ed by B. M. Trost, I. Fleming, and L. A. Paquette, Pergamon Press, Oxford (1991), Vol. 5, p. 513, and references cited therein.