Diastereoselective synthesis of protected syn 1,3-Diols: Preparation of the C16-C24 portion of dolabelides

Organic Letters

Volumn 4, Issue 3, 2002, Pages 419-421

  Grimaud, Laurence ^a   De Mesmay, Romain ^a   Prunet, Joëlle ^b  

^a Ecole Nationale Superieure de Techniques Avancees   (France)

^b LABORATOIRE DE SYNTHÈSE ORGANIQUE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

DITERPENE;

ARTICLE; CHEMICAL STRUCTURE; STEREOISOMERISM; SYNTHESIS;

DITERPENES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 0037034355     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol017122w     Document Type: Article

References (18)

1. Ojika, M.; Nagoya, T.; Yamada, K. Tetrahedron Lett. 1995, 36, 7491.
2. Suenaga, K.; Nagoya, T.; Shibata, T.; Kigoshi, H.; Yamada, K. J. Nat. Prod. 1997, 60, 155.
3. Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092.
4. For a recent use of such a coupling reaction, see: Sawada, D.; Shibasaki, M. Angew. Chem., Int. Ed. 2000, 39, 209 and references therein.
5. Evans, D. A.; Gauchet-Prunet, J. A. J. Org. Chem. 1993, 58, 2446.
6. Hoppe, D.; Zshage, O. Angew. Chem., Int. Ed. 1989, 28, 69. Zshage, O.; Hoppe, D. Tetrahedron 1992, 48, 5657.
7. Hoppe, D.; Zshage, O. Angew. Chem., Int. Ed. 1989, 28, 69. Zshage, O.; Hoppe, D. Tetrahedron 1992, 48, 5657.
8. Hoppe, D.; Hanko, R.; Brönneke, A.; Lichtenberg, F.; Van Hulsen, E. Chem. Ber. 1985, 118, 2822.
9. Prolonged exposure to 3 N HCl/THF at 65 °C cleanly gave alcohol 7.
10. Lactol 11 was also prepared by diasteresoselective epoxidation (73%, >95:5) followed by acidic hydrolysis (74%), according to: (a) Hoppe, D.; Lübmann, J.; Jones, P. G.; Schmidt, D.; Sheldrick, G. M. Tetrahedron Lett. 1986, 27, 359 1.
11. (b) Hopp, D.; Tarara, G.; Wilckens, M. Synthesis 1989, 83.
12. Hoppe, D.; Tebben, P.; Reggelin, M.; Bolte, M. Synthesis 1997, 183.
13. For a similar elimination, see ref 9.
14. Frigerio, M.; Santagostino, M. Tetrahedron Lett. 1994, 35, 8019. Frigerio, M.; Santagostino, M.; Sputore, S.; Palmisano, G. J. Org. Chem. 1995, 60, 7272.
15. Frigerio, M.; Santagostino, M. Tetrahedron Lett. 1994, 35, 8019. Frigerio, M.; Santagostino, M.; Sputore, S.; Palmisano, G. J. Org. Chem. 1995, 60, 7272.
16. Lactol 11 was also converted to compound 10 by Wittig coupling with phosphorane 2 (95%), followed by protection of the resulting diol (52%).
17. Wu, Y.; Esser, L.; De Brabander, J. K. Angew. Chem., Int. Ed. 2000, 39, 4308.
18. Kinetic resolution with 2 equiv of the crotyl carbamate at -78 °C (according to Berque, I.; Le Ménez, P.; Razon, P.; Anies, C.; Pancrazi, A.; Ardisson, J.; Neuman, A.; Prangé, T.; Brion, J.-D. Synlett 1998, 1132) produced a 1.5:1 mixture of diastereomers favoring the undesired 14dia.