A practical total synthesis of (+)-antimycin A9

Journal of Antibiotics

Volumn 60, Issue 1, 2007, Pages 65-72

  Nishii, Takeshi ^a   Inai, Makoto ^a   Kaku, Hiroto ^a   Horikawa, Mitsuyo ^a   Tsunoda, Tetsuto ^a  

^a TOKUSHIMA BUNRI UNIVERSITY   (Japan)

Author keywords

Antibiotics; Antimycin A9; Asymmetric aldol reaction; Asymmetric synthesis

Indexed keywords

ANTIMYCIN A9; CITRININ; UNCLASSIFIED DRUG; ANTIMYCIN A1; DRUG DERIVATIVE;

ALDOL REACTION; ARTICLE; BACTERIUM CULTURE; DRUG STRUCTURE; DRUG SYNTHESIS; NONHUMAN; PRIORITY JOURNAL; STREPTOMYCES; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

STREPTOMYCES SP.;

ANTIMYCIN A; MOLECULAR STRUCTURE;

EID: 34247266113     PISSN: 00218820     EISSN: None     Source Type: Journal    
DOI: 10.1038/ja.2007.9     Document Type: Article

References (18)

1. a) Bycroft DW. Dictionary of antibiotics and related substances. pp. 128, Chapman and Hall, London (1988)
2. 9, produced by Streptomyces sp. K01-0031. J Antibiot 58: 74-78 (2005)
3. 16, seven new antimycin antibiotics produced by Streptomyces spp. SPA-10191 and SPA-8893. J Antibiot 58: 460-467 (2005)
4. d) Chen G, Lin B, Lin Y, Xie F, Lu W, Fong WF. A new fungicide produced by a Streptomyces sp. GAAS7310. J Antibiot 58: 519-522 (2005) and references cited therein.
5. a) Abidi SL. High-performance liquid chromatographic separation of subcomponents of antimycin A. J Chromatogr 447: 65-79 (1988)
6. b) Abidi SL. Reversed-phase thin-layer chromatography of homologues of antimycin A and related derivatives. J Chromatogr 464: 453-458 (1989)
7. 3. J Antibiot 24: 724-726 (1971)
8. 3 and its analog. Heterocyclic Commun 6: 211-214 (2000)
9. 3b. Tetrahedron Lett 41: 7667-7671 (2000)
10. 3a. Tetrahedron Lett 44: 7829-7832 (2003)
11. 3b. J Org Chem 71: 4296-4301 (2006)
12. When the aldol reaction of 2 and 3 was carried out under the original conditions, none of the desired compound was obtained.
13. The stereochemistry of the minor adduct was presumed to be 2S,3S.
14. Oppolzer W, Blagg J, Rodriguez I, Walther E. Bornane sultam-directed asymmetric synthesis of crystalline, enantiomerically pure syn aldols. J Am Chem Soc 112: 2767-2772 (1990)
15. Oppolzer W, Lienard P. Non-destructive cleavage of N-acylsultams under neutral conditions: Preparation of enantiomerically, pure Fmoc-protected a-amino acids. Helv Chim Acta 75: 2572-2582 (1992)
16. 3. Use of the oxazole ring in protecting and activating functions. J Am Chem Soc 107: 1423-1424 (1985)
17. Inanaga J, Hirata K, Saeki H, Katsuki T, Yamaguchi M. A rapid esterification by means of mixed anhydride and its application to large-ring lactonization. Bull Chem Soc Jpn 52: 1989-1993 (1979)
18. 2·PhH.