Concise enantioselective synthesis of (+)-aspicilin based on a ruthenium catalyzed olefin metathesis reaction

Tetrahedron Letters

Volumn 39, Issue 31, 1998, Pages 5597-5600

  Nishioka, Toshiko ^a   Iwabuchi, Yoshiharu ^a   Irie, Hiroshi ^a   Hatakeyama, Susumi ^a  

^a NAGASAKI UNIVERSITY   (Japan)

Author keywords

Aspicilin; Asymmetric synthesis; Olefin metathesis; Polyol chiral building block

Indexed keywords

ALKENE; ASPICILIN; RUTHENIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHIRALITY; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; EPOXIDATION; NUCLEAR MAGNETIC RESONANCE; OXIDATION; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

EID: 0032581736     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01130-7     Document Type: Article

References (17)

1. [1] Cf.: Hanessian, S. The Total Synthesis of Natural Products: The Chiron Approach. Oxford: Pergamon Press, 1983.
2. [2] Cf.: Hanessian, S. Aldrichimica Acta 1989; 22: 3-15.
3. [3] Cf.: Lukacs G, Ohno M. (Eds.) Recent Progress in the Chemical Synthesis of Antibiotics. Berlin: Springer-Verlag, 1990.
4. [4] Hatakeyama S, Satoh K, Takano S. Tetrahedron Lett. 1993;34:7425-7428.
5. [5] Hatakeyama S, Kojima K, Fukuyama H, Irie H. Chemistry Lett. 1995:763-764.
6. [6] Esumi T, Fukuyama H, Oribe R, Kawazoe K, Iwabuchi Y, Irie H, Hatakeyama S. Tetrahedron Lett. 1997;38:4823-44826.
7. [7] Feige GB, Lumbsch HT, Huneck S, Elix JA. J. Chromatography 1993;646:417-427 and references cited therein.
8. [8] Shinha SC, Keinan E. J. Org. Chem. 1997;62:377-386 and references cited therein.
9. [9] Chênevert R, Lavoie M, Dasser M. Can. J. Chem. 1997;75:68-73.
10. [10] Kobayashi Y, Nakano M, Okui H. Tetrahedron Lett. 1997;38:8883-8886.
11. [11] For a review on olefin metathesis reactions, see: Schuster M, Blechert S. Angew. Chem. Int. Ed. Engl. 1997;36:2036-2056.
12. [12] Gao Y, Hanson RM, Klunder JM, Ko SY, Masamune H, Sharpless KB. J. Org. Chem. 1987;109:5765-5780.
13. [13] Hatakeyama S, Satoh K, Sakurai K, Takano S. Tetrahedron Lett. 1987;28:2713-2716 and 2717-2720.
14. [14] For a leading reference to macrocyclizations based on a olefin metathesis reaction, see: Nicolaou KC, He Y, Vourloumis D. Vallberg F, Roschangar F, Sarabia F, Ninkovic S, Yang Z, Trujillo JI. J. Am. Chem. Soc. 1997;119:7960-7973.
15. [15] Miller SJ, Blackwell HE, Grubbs RH. J. Am. Chem. Soc. 1996;118:9606-9614.
16. [16] Solladie G, Fernandez I, Maestro C. Tetrahedron Asymmetry 1991;2:801-817.
17. [17] Enders D, Prokopenko OF, Liebigs Ann. 1995;1185-1191.