The first total synthesis of cochleamycin A and determination of the absolute structure [2]

Journal of Antibiotics

Volumn 56, Issue 6, 2003, Pages 584-590

  Tatsuta, Kuniaki ^a   Narazaki, Fumie ^a   Kashiki, Nobusuke ^a   Yamamoto, Jun Ichiro ^a   Nakano, Satoshi ^a  

^a WASEDA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBIOTIC AGENT; COCHLEAMYCIN A; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; CONTROLLED STUDY; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; LETTER; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STREPTOMYCES; STRUCTURE ANALYSIS;

EID: 0038602926     PISSN: 00218820     EISSN: None     Source Type: Journal    
DOI: 10.7164/antibiotics.56.584     Document Type: Letter

References (15)

1. Shindo, K. & H. Kawai: Novel antibiotics, cochleamycins A and B. J. Antibiotics 45: 292-295, 1992
2. Shindo, K.; H. Iijima & H. Kawai: Studies on cochleamycins, novel antitumor antibiotics. II. Physicochemical properties and structure determination. J. Antibiotics 49: 244-248, 1996
3. Hochlowski, J. E.; M. M. Mullally, R. Henry, D. M. Whittern & J. B. McAlpine: Macquarimicins, microbial metabolites from Micromonospora. II. Isolation and structural elucidation. J. Antibiotics 48: 467-470, 1995
4. Chang, J. & L. A. Paquette: Studies aimed at the total synthesis of the antitumor antibiotic cochleamycin A. An enantioselective biosynthesis-based pathway to the AB bicyclic core. Org. Lett. 4: 253-256, 2002
5. Munakata, R.; T. Ueki, H. Katakai, K.-I. Takao & K.-I. Tadano: Synthetic study of Macquarimicins: highly stereoselective construction of the AB-ring system. Org. Lett. 3: 3029-3032, 2001
6. Tatsuta, K.; M. Itoh, R. Hirama, N. Araki & M. Kitagawa: The first total synthesis of calbistrin A, a microbial product possessing multiple bioactivities. Tetrahedron Lett. 38: 583-586, 1997
7. Tatsuta, K.; S. Yasuda, K.-I. Kurihara, K. Tanabe, R. Shinei & T. Okonogi: Total synthesis of progesterone receptor ligands, (-)-PF1092A, B and C. Tetrahedron Lett. 38: 1439-1442, 1997
8. Tatsuta, K.; S. Takano, T. Sato & S. Nakano: The first total synthesis of a macrocyclic anti-protozoan, LL-Z1640-2. Chem. Lett.: 172-173, 2001
9. Müller, S.; B. Liepold, G. J. Roth & H. J. Bestmann: An improved one-pot procedure for the synthesis of alkynes from aldehydes. Synlett: 521-522, 1996
10. Simpson, T. J.; R. W. Smith, S. M. Westaway, C. L. Willis, A. D. Buss, R. J. P. Cannell, M. J. Dawson & B. A. M. Rudd: Enantioselective synthesis of a putative hexaketide intermediate in the biosynthesis of the squalestatins. Tetrahedron Lett. 38: 5367-5370, 1997
11. Chen, K.-M.; G. E. Hardtmann, K. Prasad, O. Repic & M. J. Shapiro: 1,3-Syn diastereoselective reduction of β-hydroxyketones utilizing alkoxydialkylboranes. Tetrahedron Lett. 28: 155-158, 1987
12. Boden, C. D. J.; G. Pattenden & T. Ye: Palladium-catalysed hydrostannylations of 1-bromoalkynes. A practical synthesis of (E)-1-stannylalk-1-enes. J. Chem. Soc., Perkin Trans. 1: 2417-2419, 1996
13. Takeda, K.; E. Kawanishi, H. Nakamura & E. Yoshii: Total synthesis of tetronolide, the aglycon of tetrocarcins. Tetrahedron Lett. 32: 4925-4928, 1991
14. 2-induced cyclization of ω-(α-bromoacyloxy) aldehydes. Tetrahedron Lett. 27: 3889-3890, 1986
15. Kita, Y.; H. Maeda, K. Omori, T. Okuno & Y. Tamura: Novel efficient synthesis of 1-ethoxyvinyl esters using ruthenium catalysts and their use in acylation of amines and alcohols: synthesis of hydrophilic 3′-N-acylated oxaunomycin derivatives. J. Chem. Soc., Perkin Trans. 1: 2999-3005, 1993