Concise Synthesis of (±)-Perovskone

Journal of the American Chemical Society

Volumn 116, Issue 11, 1994, Pages 4979-4980

  Majetich, George ^a   Zhang, Yong ^a  

^a UNIVERSITY OF GEORGIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PEROVSKONE; TRITERPENE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; SYNTHESIS;

EID: 0028086375     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00090a050     Document Type: Article

References (13)

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2. Ahmad and co-workers have postulated the following biogenesis for perovskone. See also: Watson, W. H.; Taira, Z. Tetrahedron Lett. 1976, 2501.
3. St. Jacques, M.; Vaziri, C. Org. Magn. Resort. 1972, 4, 77.
4. Majetich, G.; Zhang, Y.; Feltman, T. L.; Duncan, S. G., Jr. Tetrahedron Lett. 1993, 34, 445.
5. Majetich, G.; Zhang, Y.; Feltman, T. L.; Belfoure, V. Tetrahedron Lett. 1993, 34, 441.
6. Dorn, H. W.; Warren, W. H.; Bullock, J. C. J. Am. Chem. Soc. 1939, 61, 145.
7. Stetter, H.; Dierichs, W. Chem. Ber. 1952, 85, 1061.
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11. trans-β-Ocimene is thermally stable and does not isomerize to its various allocimene isomers. See: Wolinsky, J.; Chollar, B.; Baird, M. D. J. Am. Chem. Soc. 1962, 84, 2775.
12. Gandhi, R. P.; Ishar, M. P. S.; Wali, A. J. Chem. Soc, Chem. Comm. 1988, 1074.
13. In our hands the reaction of geranyl pyrophosphate with quinone 2 fails, undoubtedly because this ester decomposes to form a complex mixture of acyclic and cyclic terpenes. See: Haley, R. C.; Miller, J. A.; Wood, H. C. S. J. Chem. Soc. (C) 1969, 264.