Wittig reaction: A new route to α-methoxyketones. Application to the synthesis of simplified analogs of artemisinin

Tetrahedron Letters

Volumn 39, Issue 23, 1998, Pages 4029-4030

  Hamzaoui, Mohamed ^a   Provot, Olivier ^a   Camuzat Dedenis, Boris ^a   Moskowitz, Henri ^a   Mayrargue, Joëlle ^a   Cicéron, Liliane ^b   Gay, Frédérick ^b  

^a UNIVERSITÉ PARIS SACLAY   (France)

^b PITIÉ SALPÊTRIÈRE HOSPITAL   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA METHYLKETONE; ARTEMISININ; NITRILE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS; STRUCTURE ANALYSIS;

EID: 0032482483     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00688-1     Document Type: Article

References (9)

1. 1. Klayman, D. L. Science 1995, 228, 1049-1055.
2. 2. Brossi, A.; Venugopalan, B.; Dominguez Gerp, L.; Yeh, H.J.C.; Flippen-Anderson, J.L.; Buchs, P.; Luo, X.D.; Milhous, W.; Peters, W. J. Med. Chem. 1988, 31, 645-650.
3. 3. Avery, M. A.; Mehrotra, S.; Bonk, J. D.; Vroman, J. A.; Goins, D. K.; Miller, R. J. Med. Chem. 1996,39, 2900-2906.
4. 4. Provot, O.; Hamzaoui, M.; Nguyen Huy, D.; Mayrargue, J.; Moskowitz, H. Heterocyclic Commun. 1996, 3, 267-271.
5. 5. Hamzaoui, M.; Provot, O.; Grégoire, F.; Riche, C.; Chiaroni, A.; Gay, F.; Moskowitz, H.; Mayrargue, J. Tetrahedron : Asymmetry 1997, 13, 2085-2088.
6. 6. Newman, M. S.; Beal, P. F. J. Am. Chem. Soc. 1950, 72, 5161-5163.
7. 7. Moriarty, R. M.; Prakash, I.; Penmastra, R. Synthetic Commun., 1987, 17, 709-714.
8. 8. Barnhardt, R. G.; McEwen, W. J. Am. Chem. Soc. 1967, 26, 7009-7014.
9. 9. Typical General Procedure: To a 0°C cooled solution of 3.5 g (10 mmol) of methoxymethyltriphenylphosphonium chloride in dry THF (50 ml) were added dropwise 10 mmol of Phli. The red solution was stirred at 0°C for two hours and 2.5 mmol of nitrile in 10 ml of THF were added slowly. After the reaction was completed, as juged by TLC, the solution was pourred into water and extracted with ether.