Formal enantiospecific synthesis of (+)-FR900482

Journal of Organic Chemistry

Volumn 68, Issue 1, 2003, Pages 130-138

  Paleo, M Rita ^a,b   Aurrecoechea, Natalia ^a   Jung, Kang Yeoun ^a   Rapoport, Henry ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROXYMETHYLATION;

ANTIBIOTICS; CONDENSATION; NITROGEN; OXIDATION; SYNTHESIS (CHEMICAL); TUMORS; X RAY CRYSTALLOGRAPHY;

AROMATIC COMPOUNDS;

1 ACETYL 8ALPHA (CARBAMOYLOXYMETHYL) 3,9 EPOXY 5 FORMYL 1,1A,2,8,9,9A OCTAHYDROAZIRINO[2,3 C][1]BENZAZOCINE 7,9 DIOL ACETATE; 4 FORMYL 6,9 DIHYDROXY 14 OXA 1,11 DIAZATETRACYCLO[7.4.1.0 2,7 0 10,12]TETRADECA 2,4,6 TRIEN 8 YLMETHYLCARBAMATE; ACETIC ACID; ACID; AMINOALCOHOL; ANILINE; AROMATIC AMINE; AZIRIDINE; EPOXIDE; HYDROXYL GROUP; HYDROXYLAMINE; NITROGEN; PHTHALIC ACID DIMETHYL ESTER;

ARTICLE; CARBAMOYLATION; CHIRALITY; DRUG STRUCTURE; DRUG SYNTHESIS; ELECTROCHEMICAL ANALYSIS; ENANTIOMER; EPOXIDATION; HYDROXYLATION; METHYLATION; OXIDATION; POLYMERIZATION; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

ANTIBIOTICS, ANTINEOPLASTIC; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; CRYSTALLOGRAPHY, X-RAY; EPOXY COMPOUNDS; GLYCINE; MOLECULAR STRUCTURE; OXAZINES; OXIDATION-REDUCTION; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0037427994     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0206521     Document Type: Article

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38. Total synthesis of natural (+)-FR900482: (a) Katoh, T.; Itoh, E.; Yoshino, T.; Terashima, S. Tetrahedron Lett. 1996, 37, 3471. (b) Yoshino, T.; Nagata, Y.; Itoh, E.; Hashimoto, M.; Katoh, T.; Terashima, S. Tetrahedron Lett. 1996, 37, 3475. (c) Katoh, T.; Yoshino, T.; Nagata, Y.; Nakatani, S.; Terashima, S. Tetrahedron Lett. 1996, 37, 3479. Total synthesis of an enantiomeric pair of FR900482: (d) Katoh, T.; Itoh, E.; Yoshino, T.; Terashima, S. Tetrahedron 1997, 53, 10229. (e) Yoshino, T.; Nagata, Y.; Itoh, E.; Hashimoto, M.; Katoh, T.; Terashima, S. Tetrahedron 1997, 53, 10239. (f) Katoh, T.; Nagata, Y.; Yoshino, T.; Nakatani, S.; Terashima, S. Tetrahedron 1997, 53, 10253. (g) For the enantioselective synthesis of FR900482 analogues see: Kambe, M.; Arai, E.; Suzuki, M.; Tokuyama, H.; Fukuyama, T. Org. Lett. 2001, 3, 2575.
39. Total synthesis of natural (+)-FR900482: (a) Katoh, T.; Itoh, E.; Yoshino, T.; Terashima, S. Tetrahedron Lett. 1996, 37, 3471. (b) Yoshino, T.; Nagata, Y.; Itoh, E.; Hashimoto, M.; Katoh, T.; Terashima, S. Tetrahedron Lett. 1996, 37, 3475. (c) Katoh, T.; Yoshino, T.; Nagata, Y.; Nakatani, S.; Terashima, S. Tetrahedron Lett. 1996, 37, 3479. Total synthesis of an enantiomeric pair of FR900482: (d) Katoh, T.; Itoh, E.; Yoshino, T.; Terashima, S. Tetrahedron 1997, 53, 10229. (e) Yoshino, T.; Nagata, Y.; Itoh, E.; Hashimoto, M.; Katoh, T.; Terashima, S. Tetrahedron 1997, 53, 10239. (f) Katoh, T.; Nagata, Y.; Yoshino, T.; Nakatani, S.; Terashima, S. Tetrahedron 1997, 53, 10253. (g) For the enantioselective synthesis of FR900482 analogues see: Kambe, M.; Arai, E.; Suzuki, M.; Tokuyama, H.; Fukuyama, T. Org. Lett. 2001, 3, 2575.
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42. Total synthesis of natural (+)-FR900482: (a) Katoh, T.; Itoh, E.; Yoshino, T.; Terashima, S. Tetrahedron Lett. 1996, 37, 3471. (b) Yoshino, T.; Nagata, Y.; Itoh, E.; Hashimoto, M.; Katoh, T.; Terashima, S. Tetrahedron Lett. 1996, 37, 3475. (c) Katoh, T.; Yoshino, T.; Nagata, Y.; Nakatani, S.; Terashima, S. Tetrahedron Lett. 1996, 37, 3479. Total synthesis of an enantiomeric pair of FR900482: (d) Katoh, T.; Itoh, E.; Yoshino, T.; Terashima, S. Tetrahedron 1997, 53, 10229. (e) Yoshino, T.; Nagata, Y.; Itoh, E.; Hashimoto, M.; Katoh, T.; Terashima, S. Tetrahedron 1997, 53, 10239. (f) Katoh, T.; Nagata, Y.; Yoshino, T.; Nakatani, S.; Terashima, S. Tetrahedron 1997, 53, 10253. (g) For the enantioselective synthesis of FR900482 analogues see: Kambe, M.; Arai, E.; Suzuki, M.; Tokuyama, H.; Fukuyama, T. Org. Lett. 2001, 3, 2575.
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