Enantioselective total synthesis of the (-)-(6R,11R,14S)-isomer of colletallol

Journal of Organic Chemistry

Volumn 62, Issue 18, 1997, Pages 6374-6378

  Amigoni, Sonia J ^a   Toupet, Loïc J ^b   Le Floc'h, Yves J ^a  

^a Laboratoire de Synthèse et Activation des Biomolécules   (France)

^b UNIVERSITÉ DE RENNES 1   (France)

Author keywords

[No Author keywords available]

Indexed keywords

COLLETALLOL; MACROCYCLIC COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; GENE TARGETING; MOLECULAR INTERACTION; NONHUMAN; PROTEIN FAMILY; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0030765131     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970020s     Document Type: Article

References (19)

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2. For full documentation about macrodiolides up to 1905, see: Amigoni, S. J. Ph.D. Thesis, Rennes I University, 1996,
3. and Le Floc'h, Y.; Dumartin, H.; Grée R. Bull. Soc. Chim. Fr. 1995, 232, 114-118.
4. Hanson, K.; O'Neill, J. A.; Simpson, T. J.; Willis, C. L. J. Chem. Soc., Perkin Trans. 1 1994, 2493-2497.
5. Yvergnaux, F.; Le Floc'h, Y.; Grée, R. Tetrahedron Lett. 1989, 30, 7397-7398. Le Floc'h, Y.; Yvergnaux, F.; Grée, R. Bull. Soc. Chim. Fr. 1992, 129, 62-70.
6. Yvergnaux, F.; Le Floc'h, Y.; Grée, R. Tetrahedron Lett. 1989, 30, 7397-7398. Le Floc'h, Y.; Yvergnaux, F.; Grée, R. Bull. Soc. Chim. Fr. 1992, 129, 62-70.
7. Dumartin, H.; Le Floc'h, Y.; Grée, R. Tetrahedron Lett. 1994, 35, 6681-6684. Contrary to an earlier report from one of us, the reduction of enone 2 with the (S)-CBS reagent gave an allylic alcohol with (S)-configuration; the right columns of Tables 1 and 2 in the cited article thus concern the ratio 7/6 and not 6/7.
8. Dommerholt, L. J.; Thijs, L.; Zwanenburg, B. Tetrahedron Lett. 1991, 32, 1495-1498.
9. Corey, E. J.; Link, J. O. Tetrahedron Lett. 1992, 33, 4141-4144.
10. Corey, E. J.; Bakshi, R. K. Tetrahedron Lett. 1990, 37, 611-614.
11. Corey, E. J.; Azimioara, M.; Sarshar, S. Tetrahedron Lett. 1992, 33, 3429-3430.
12. the p-methoxyphenyl group has been used in order to protect some primary alcohols: Fukuyama, T.; Laird, A. A.; Hotchkiss, L. M. Tetrahedron Lett. 1985, 26, 6291-6292. Petitou, M.; Duchaussoy, P.; Choay, J. Tetrahedron Lett. 1988, 29, 1389-1390. To our knowledge, this is the first time that this group has been used for the protection of a secondary alcohol.
13. the p-methoxyphenyl group has been used in order to protect some primary alcohols: Fukuyama, T.; Laird, A. A.; Hotchkiss, L. M. Tetrahedron Lett. 1985, 26, 6291-6292. Petitou, M.; Duchaussoy, P.; Choay, J. Tetrahedron Lett. 1988, 29, 1389-1390. To our knowledge, this is the first time that this group has been used for the protection of a secondary alcohol.
14. Corey, E. J.; Link, J. O. Tetrahedron Lett. 1992, 33, 3431-3434.
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19. The author has deposited atomic coordinates for structures 1 and 13 with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, U.K.