Synthesis of isovalerenenol, a sesquiterpene alcohol isolated from a soft coral and the stability of related hydrindanone derivatives

Tetrahedron

Volumn 52, Issue 30, 1996, Pages 9999-10010

  Tori, Motoo ^a   Ikawa, Masayo ^a   Sagawa, Tetsuya ^a   Furuta, Hirosuke ^a   Sono, Masakazu ^a   Asakawa, Yoshinori ^a  

^a TOKUSHIMA BUNRI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ISOVALERENOL; SESQUITERPENE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030598039     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00544-3     Document Type: Article

References (14)

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2. 2 Honda, T.; Ishige, H.; Tsubuki, M.; Naito K.; Suzuki, Y. J. Chem. Soc., Perkin Trans. 1, 1991, 954-955; Honda, T.; Ishige, H.; Tsubuki, M.; Naito K.; Suzuki, Y. Chem. Pharm. Bull., 1991, 39, 1641-1643.
3. 2 Honda, T.; Ishige, H.; Tsubuki, M.; Naito K.; Suzuki, Y. J. Chem. Soc., Perkin Trans. 1, 1991, 954-955; Honda, T.; Ishige, H.; Tsubuki, M.; Naito K.; Suzuki, Y. Chem. Pharm. Bull., 1991, 39, 1641-1643.
4. 3 Blumenkopf, T. A.; Heathcock, C. H. J. Am. Chem. Soc., 1983, 105, 2354-2358.
5. 1 were used throughout the work.
6. 5 The authentic trans hydrindanone 3t was prepared in three steps from 5. The 1,4-addition of 4-chloro-2-methyl-1-butene to 5 in the presence of CuI afforded trans product 20 in 80% yield. Ozonolysis and aldol cyclization gave 3t in 82% yield. (Equation presented)
7. 6 Because the product had a double bond between C-5 and C-6, the stereochemistry at C-4 was not determined.
8. 7 Majetich, G.; Condon, S.; Hull, K.; Ahmad, S. Tetrahedron Lett., 1989, 30, 1033-1036.
9. 8 Cicero, B. L.; Weisbuch F.; Dana, G. J. Org. Chem., 1981, 46, 914-919 (1981); Peterson, P. E.; Leffew, R. L. B.; Jensen, B. L. J. Org. Chem., 1986, 51, 1948-1954; House, H. O.; Rasmusson, G. H. J. Org. Chem., 1963, 28, 31-34.
10. 8 Cicero, B. L.; Weisbuch F.; Dana, G. J. Org. Chem., 1981, 46, 914-919 (1981); Peterson, P. E.; Leffew, R. L. B.; Jensen, B. L. J. Org. Chem., 1986, 51, 1948-1954; House, H. O.; Rasmusson, G. H. J. Org. Chem., 1963, 28, 31-34.
11. 8 Cicero, B. L.; Weisbuch F.; Dana, G. J. Org. Chem., 1981, 46, 914-919 (1981); Peterson, P. E.; Leffew, R. L. B.; Jensen, B. L. J. Org. Chem., 1986, 51, 1948-1954; House, H. O.; Rasmusson, G. H. J. Org. Chem., 1963, 28, 31-34.
12. 9 CONFLEX Ver. 3.45, by H. Goto and E. Ôsawa, Department of Knowledge-Based Information Engineering, Toyohashi University of Technology, Toyohashi 441, Japan; Goto, H.; Ôsawa, E. Tetrahedron Lett., 1992, 33, 1343-4346; Goto, H.; Ôsawa, E. J. Chem. Soc., Perkin Trans 2, 1993, 187-198.
13. 9 CONFLEX Ver. 3.45, by H. Goto and E. Ôsawa, Department of Knowledge-Based Information Engineering, Toyohashi University of Technology, Toyohashi 441, Japan; Goto, H.; Ôsawa, E. Tetrahedron Lett., 1992, 33, 1343-4346; Goto, H.; Ôsawa, E. J. Chem. Soc., Perkin Trans 2, 1993, 187-198.
14. 9 CONFLEX Ver. 3.45, by H. Goto and E. Ôsawa, Department of Knowledge-Based Information Engineering, Toyohashi University of Technology, Toyohashi 441, Japan; Goto, H.; Ôsawa, E. Tetrahedron Lett., 1992, 33, 1343-4346; Goto, H.; Ôsawa, E. J. Chem. Soc., Perkin Trans 2, 1993, 187-198.