Synthesis of monoterpenic analogues of puupehenone and puupehedione

Tetrahedron Letters

Volumn 39, Issue 16, 1998, Pages 2425-2428

  Barrero, Alejandro F ^a   Alvarez Manzaneda, Enrique J ^a   Herrador, M Mar ^a   Valdivia, Mónica V ^a   Chahboun, Rachid ^a  

^a UNIVERSITY OF GRANADA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; PUUPEHEDIONE; PUUPEHENONE; TERPENE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; HUMAN; HUMAN CELL; NONHUMAN; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0032537094     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00216-0     Document Type: Article

References (9)

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2. 2. Navi, B.N.; Perzanowski, H.P.; Ross, R.A.; Erdman, T.R.; Scheuer, P.J.; Finer, J.; Clardy, J. Pure Appl. Chem. 1979, 51, 1893-1900.
3. 3. Nasu, S.S.; Yeung, B.K.S.; Hamann, M.T.; Scheuer, P.J.; Kelly-Borges, M.; Goins, K., J. Org. Chem. 1995, 60, 7290-7292.
4. 4. Sarin, P.S.; Sun, D.; Thorton, A.; Muller, W.E.G. J. Nat. Cancer Inst. 1987, 78, 663-665.
5. 5. Barrero, A. F.; Alvarez-Manzaneda, E. ; Chahboun, R.; Tetrahedron Letters 1997, 38, 1525-1528.
6. 6. Arjona, O.; Garranzo, M.; Mahugo, J.; Maroto, E.; Plumet, J.; Sáez, Tetrahedron Letters 1997, 38, 7249-7252.
7. 5
8. 8. Illustrative experimental procedure for the oxidative rupture: To a stirred solution of 180 mg (o.66 mmol) of 15 in 10 ml of dry 1,4-dioxane was added 115 mg (0.66 mmol) of TsOH and 300 mg (1.32 mmol) of DDQ and he mixture was heated under reflux for 2h . After removal of the 1,4-dioxane in vacuo, the remaining solid was chromatographed on a silica gel column (Hexane-Diethyl Ether 1:1) to afford 134 mg (79%) of 8.
9. 2), 47.9 (CH), 82.2 (C), 108.1 (CH), 128.3 (CH), 145.3 (C), 165.4 (C), 178.9 (C), 180.5 (C).