A preparative synthesis of lapachol and related naphthoquinones

Tetrahedron Letters

Volumn 39, Issue 45, 1998, Pages 8221-8224

  Sun, Jerry S ^a   Geiser, Andrew H ^b   Frydman, Benjamin ^a  

^a SLIL Biomedical Corp   (United States)

^b UNIVERSITY OF WISCONSIN SCHOOL OF MEDICINE AND PUBLIC HEALTH   (United States)

Author keywords

Alkenyl halides; Antitumor compounds; Lithium hydride; Quinones

Indexed keywords

1,4 BENZOQUINONE; 1,4 NAPHTHOQUINONE DERIVATIVE; 3 HYDROXY BETA LAPACHONE; CARBOXYLIC ACID DERIVATIVE; DIMETHYL SULFOXIDE; LAPACHOL; LITHIUM; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CYCLIZATION; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0032487876     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01880-2     Document Type: Article

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14. 3, 300 MHz) δ 8.12 (d, J = 7.5 Hz, 1H), 8.07 (d, J = 7.5 Hz, 1H), 7.75 (t, J = 7.5 Hz, 1H), 7.67 (t, J = 7.5 Hz, 1H), 7.29 (s, 1H), 5.21 (t, J = 7.3 Hz, 2H), 3.31 (d, J = 7.3 Hz, 1H), 1.79 (s, 3H), 1.68 (s, 3H).
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16. 3) δ 8.06 (d, J = 7.6 Hz, 1H), 7.84 (d, J = 7.6 Hz, 1H), 7.66 (t, J = 7.6 Hz, 1H), 7.52 (t, J = 7.6 Hz, 1H), 3.92 (m, 1H), 2.83 (dd, J = 17.7, 4.8 Hz, 1H), 2.62 (dd, J = 17.7, 5.4 Hz, 1H), 1.52 (s, 3H),1.46 (s, 3H).
17. 17. Singh, P.; Pardasani, R.T.; Suri, A.; Pokharna, C.P. Zeit. Naturforsch. 1992, 47b, 1031-1033.
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19. 3) δ 8.10 (d, 1H), 7.84 (d, 1H), 7.68 (t, 1H), 7.55 (t, 1H), 5.22 (t, 1H), 3.33 (s, 2H), 2.95 (dd, 1H), 2.74 (dd, 1H), 1.52 (d, 6H), 1.42 (s, 9H).
20. +).
21. +).
22. +).
23. 23. Cooke, R.G. Austr. J. Sci. Res.(A) 1950, 3, 481-494.