Process-scale total synthesis of nature-identical (-)-(S,S)-7- hydroxycalamenal in high enantiomeric purity through catalytic enantioselective hydrogenation

Helvetica Chimica Acta

Volumn 88, Issue 7, 2005, Pages 1776-1789

  Benincori, Tiziana ^a   Bruno, Silvana ^b   Celentano, Giuseppe ^c   Pilati, Tullio ^d   Ponti, Alessandro ^d   Rizzo, Simona ^d   Sada, Mara ^e   Sannicolò, Francesco ^d,e  

^a UNIVERSITY OF INSUBRIA   (Italy)

^b INSTM   (Italy)

^c Ist di Chim Organ A Marchesini   (Italy)

^d CNR   (Italy)

^e Dipartimento di Chimica Organica e Industriale   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; COMPLEXATION; COMPUTATIONAL METHODS; CONFORMATIONS; CRYSTALLIZATION; SYNTHESIS (CHEMICAL);

COMPUTATIONAL CONFORMATION ANALYSIS; DIASTEREOSELECTIVITY; OPTICAL PURITY; STEREOSELECTIVE SYNTHESIS;

HYDROGENATION;

2 (4 METHOXYPHENYL) 3 METHYLBUT 2 ENOIC ACID; 3,4 DIHYDRO 4 (1 METHYLETHYL) 7 METHOXY 2H NAPHTHALEN 1 ONE; 5,6,7,8 TETRAHYDRO 3 HYDROXY 5 METHYL 8 (1 METHYLETHYL)NAPHTHALENE 2 CARBALDEHYDE; 7 HYDROXYCALAMENAL; NAPHTHALENE DERIVATIVE; SESQUITERPENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHIRALITY; CONFORMATION; CRYSTALLIZATION; ENANTIOMER; ENANTIOSELECTIVITY; HYDROGENATION; PRIORITY JOURNAL; SYNTHESIS;

EID: 23044460006     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/hlca.200590139     Document Type: Article

References (35)

1. M. Frachebond, J. W. Rowe, R. W. Scott, S. M. Fanega, A. J. Buhl, J. K. Toda, Forest Prod. J. 1968, 18, 37;
2. B. O. Lindgren, C. M. Svhan, Phytochemistry 1968, 7, 1407.
3. R. S. Burden, M. S. Kemp, Phytochemistry 1984, 23, 383.
4. J. Belavadi, S. N. Kulkarni, Ind. J. Chem., Sect. B 1978, 16, 747.
5. J. W. Rowe, J. K. Toda, Chem. Ind. 1969, 27, 922;
6. J. W. Rowe, M. K. Seikel, D. N. Roy, E. Jorgensen, Phytochemistry 1972, 11, 2513;
7. K. Nabeta, K. Katayama, S. Nakagawara, K. Katoh, Phytochemistry 1993, 32, 117.
8. F. Bohlmann, W. Mailahn, Chem. Ber. 1981, 114, 1091;
9. K. Takaki, M. Okada, M. Yamada, K. Negoro, J. Org. Chem. 1982, 47, 1200;
10. M. Uemura, K. Isobe, K. Take, Y. Hayashi, J. Org. Chem. 1983, 48, 3855;
11. K. Takaki, M. Okada, M. Yamada, K. Negoro, J. Chem. Soc., Perkin Trans, 1 1984, 741;
12. M. Uemura, K. Isobe, Y. Hayashi, Chem. Lett. 1985, 91;
13. J. Tanaka, M. Takashi, N. Iwasaki, K. Adachi, Bull. Chem. Soc. Jpn. 1992, 2851.
14. J. Alexander, K. G. S. Rao, Tetrahedron 1971, 27, 645.
15. K. Tanaka, S. Quiao, M. Tobisu, M. M.-C. Lo, G. C. Fu, J. Am. Chem. Soc. 2000, 122, 9870.
16. T. Sakamoto, F. Shiga, A. Yasuhara, D. Uchiyama, Y. Kondo, H., Yamanaka, Synthesis 1992, 746.
17. E. Brenna, S. Dei Negri, C. Fuganti, F. G. Gatti, S. Serra, Tetrahedron: Asymmetry 2004, 15, 335.
18. W. S. Johnson, L. Werthemann, W. R. Bartlett, T. J. Broksom, T.-T. Li, J. Am. Chem. Soc. 1970, 92, 741.
19. R. Raap, C. G. Chin, R. G. Micetich, Can. J. Chem. 1971, 49, 2143.
20. T. Benincori, E. Brenna, F. Sannicolò, L. Trimarco, P. Antognazza, E. Cesarotti, F. Demartin, T. Pilati, J. Org. Chem. 1996, 61, 6244;
21. T. Benincori, E. Cesarotti, O. Piccolo, F. Sannicolò, J. Org. Chem. 2000, 65, 2043;
22. T. Benincori, S. Rizzo, F. Sannicolò, J. Heterocycl. Chem. 2002, 39, 471.
23. T. Benincori, O. Piccolo, S. Rizzo, F. Sannicolò, J. Org. Chem. 2000, 65, 8340.
24. L. F. Tietze, K. Thede, R. Schimpf, F. Sannicolò, Chem. Commun. 1999, 1811;
25. L. F. Tietze, K. Thede, F. Sannicolò, Chem. Commun. 2000, 583.
26. T. Benincori, T. Pilati, S. Rizzo, F. Sannicolò, J. Org. Chem., submitted;
27. F. Sannicolò, O. Piccolo, T. Benincori, M. Sada, A. Verrazzani, S. Tollis, E. Ullucci, L. De Ferra, S. Rizzo, to Chemi S.p.A., Italy, WO patent 03074169; EP 1490173.
28. I. Takemoto, N. Kawamura, H. Kaminaka, Biotech. Biochem. 1994, 58, 2071.
29. T. Hayashi, N. Kawamura, Y. Ito, J. Am. Chem. Soc. 1987, 109, 7876.
30. P. Antognazza, T. Benincori, E. Brenna, E. Cesarotti, F. Sannicolò, L. Trimarco, to Chemi S.p.A., Italy, US Patents 5,907,045 (1999); 6,077,958 (2000); 6,133,191 (2000); 6,297,387 B1 (2001); 6,297,387 B1 (2001); and 6,586,357 B1 (2003).
31. O. Mitsunobu, Synthesis 1981, 1.
32. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. J. A. Montgomery, R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, N. Rega, P. Salvador, J. J. Dannenberg, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, A. G. Baboul, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, J. L. Andres, C. Gonzalez, M. Head-Gordon, E. S. Replogle, J. A. Pople, Gaussian 98, Revision A.11.3, Gaussian, Inc., Pittsburgh, 2002.
33. M. C. Burla, M. Camalli, B. Carrozzini, G. L. Cascarano, C. Giacovazzo, G. Polidori, R. Spagna, J. Appl. Crystallogr. 2003, 36, 1103.
34. G. M. Sheldrick, SHELX97, Program for the Refinement of Crystal Structures, University of Göttingen, Germany, 1997.
35. M. N. Burnett, C. K. Johnson, Report ORNL-6895, Oak Ridge National Laboratory, Tennessee, USA, 1996.