Construction of AB-ring system of taxane framework by A-ring annulation strategy: Synthesis of 1-hydroxy-8,11,11-trimethylbicyclo[5.3.1]undec-7-en- 9-one by way of intramolecular aldol cyclization to form the C1-C10 bond

Chemical and Pharmaceutical Bulletin

Volumn 45, Issue 12, 1997, Pages 1898-1905

  Yamada, Koji ^a   Iwadare, Hayato ^a   Mukaiyama, Teruaki ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

1 hydroxy 8,11,11 trimethylbicyclo 5.3.1 undec 7 en 9 one; A ring annulation strategy; Bicyclic lactone; Intramolecular aldol reaction; Taxane AB ring system; Tetra substituted alkene

Indexed keywords

1 HYDROXY 8,11,11 TRIMETHYLBICYCLO[5.3.1] UNDEC 7 EN 9 ONE; TAXANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BINDING KINETICS; CHEMICAL REACTION KINETICS; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; MEDICINAL PLANT; STRUCTURE ANALYSIS;

EID: 0031443257     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.45.1898     Document Type: Article

References (24)

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3. Paclitaxel is the generic name for taxol, which is now a registered trademark.
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11. Other A-ring annulations in synthetic studies of taxanes: Swindell C. S., Patel B. P., Tetrahedron Lett., 28, 5275-5278 (1987); idem, J. Org. Chem., 55, 3-5 (1990); Magnus P., Booth J., Diorazio L., Donohoe T., Lynch V., Magnus N., Mendoza J., Pye P., Tarrant J., Tetrahedron, 52, 14103-14146 (1996); synthesis of bicyclo[5.3.1]undec-7-en-9-one: House H. O., Sieloff R. F., Lee T. V., DeTar M. B., J. Org. Chem., 45, 1800-1806 (1980).
12. Other A-ring annulations in synthetic studies of taxanes: Swindell C. S., Patel B. P., Tetrahedron Lett., 28, 5275-5278 (1987); idem, J. Org. Chem., 55, 3-5 (1990); Magnus P., Booth J., Diorazio L., Donohoe T., Lynch V., Magnus N., Mendoza J., Pye P., Tarrant J., Tetrahedron, 52, 14103-14146 (1996); synthesis of bicyclo[5.3.1]undec-7-en-9-one: House H. O., Sieloff R. F., Lee T. V., DeTar M. B., J. Org. Chem., 45, 1800-1806 (1980).
13. Other A-ring annulations in synthetic studies of taxanes: Swindell C. S., Patel B. P., Tetrahedron Lett., 28, 5275-5278 (1987); idem, J. Org. Chem., 55, 3-5 (1990); Magnus P., Booth J., Diorazio L., Donohoe T., Lynch V., Magnus N., Mendoza J., Pye P., Tarrant J., Tetrahedron, 52, 14103-14146 (1996); synthesis of bicyclo[5.3.1]undec-7-en-9-one: House H. O., Sieloff R. F., Lee T. V., DeTar M. B., J. Org. Chem., 45, 1800-1806 (1980).
14. Other A-ring annulations in synthetic studies of taxanes: Swindell C. S., Patel B. P., Tetrahedron Lett., 28, 5275-5278 (1987); idem, J. Org. Chem., 55, 3-5 (1990); Magnus P., Booth J., Diorazio L., Donohoe T., Lynch V., Magnus N., Mendoza J., Pye P., Tarrant J., Tetrahedron, 52, 14103-14146 (1996); synthesis of bicyclo[5.3.1]undec-7-en-9-one: House H. O., Sieloff R. F., Lee T. V., DeTar M. B., J. Org. Chem., 45, 1800-1806 (1980).
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