Synthetic studies on highly oxygenated quassinoids: Total synthesis of (±)-14β,15β-dihydroxyklaineanone

Tetrahedron Letters

Volumn 37, Issue 16, 1996, Pages 2699-2702

  Grieco, Paul A ^a   Cowen, Scott D ^a   Mohammadi, Farahnaz ^a  

^a INDIANA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

14BETA,15BETA DIHYDROXYKLAINEANONE; QUASSINOID; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029960768     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00340-1     Document Type: Article

References (6)

1. Monta, H.; Kishi, E.; Takeya, K.; Itokawa, H.; Tanaka, O., Chem. Lett. 1990, 749-752.
2. (a) Grieco, P.A.; Parker, D.T.; Nargund, R.P., J. Am. Chem. Soc. 1988, 110, 5568-5569.
3. (b) Grieco, P.A.; Nargund, R.P., Parker, D.T., J. Am. Chem. Soc. 1989, 111, 6287-6294.
4. For the use of tetra-n-butylammonium fluoride in the dehydrobromination of similar systems see: Moher, E.D.; Collins, J.L.; Grieco, P.A., J. Am. Chem. Soc. 1992, 114, 2764-2765. Grieco, P.A.; Piñeiro-Nuñez, M.M., J. Am. Chem. Soc. 1994, 116, 7606-7615.
5. For the use of tetra-n-butylammonium fluoride in the dehydrobromination of similar systems see: Moher, E.D.; Collins, J.L.; Grieco, P.A., J. Am. Chem. Soc. 1992, 114, 2764-2765. Grieco, P.A.; Piñeiro-Nuñez, M.M., J. Am. Chem. Soc. 1994, 116, 7606-7615.
6. Use of a saturated sodium potassium tartrate solution in the work-up of the demethylation reaction employing boron tribromide proved critical. In its absence no product could be isolated, presumably because the 14β,15β-diol unit of 1 sequesters the boron as a mixed borate ester which does not fall apart upon exposure to aqueous sodium bicarbonate.