Catalytic asymmetric synthesis of a potent thiomarinol antibiotic

Journal of the American Chemical Society

Volumn 127, Issue 6, 2005, Pages 1628-1629

  Gao, Xuri ^a   Hall, Dennis G ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBIOTIC AGENT; PSEUDOMONIC ACID; STREPTOMYCIN; TETRACYCLINE; THIOMARINOL; UNCLASSIFIED DRUG;

ALTEROMONAS; ARTICLE; ASYMMETRIC CATALYSIS; ASYMMETRIC SYNTHESIS; CHEMICAL STRUCTURE; CYCLOADDITION; DRUG ABSORPTION; DRUG BIOAVAILABILITY; NONHUMAN; OLEFINATION; SKIN INFECTION; STEREOCHEMISTRY;

ALTEROMONAS; ANTI-BACTERIAL AGENTS; CATALYSIS; MUPIROCIN; PYRANS; STEREOISOMERISM;

EID: 13644255983     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja042827p     Document Type: Article

References (19)

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13. These reactions are further complicated by difficulties in making isomerically pure 2-substituted acyclic enol ethers. For examples of catalytic enantioselective HDA reactions of cyclic enol ethers, see: (a) Evans, D. A.; Johnson, J. S.; Olhava, E. J. J. Am. Chem. Soc. 2000, 122, 1635-1649. (b) Audrain, H.; Thorauge, J.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 2000, 65, 4487-4497.
14. These reactions are further complicated by difficulties in making isomerically pure 2-substituted acyclic enol ethers. For examples of catalytic enantioselective HDA reactions of cyclic enol ethers, see: (a) Evans, D. A.; Johnson, J. S.; Olhava, E. J. J. Am. Chem. Soc. 2000, 122, 1635-1649. (b) Audrain, H.; Thorauge, J.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 2000, 65, 4487-4497.
15. See Supporting Information for more details and references on the preparation of this compound.
16. 6
17. 3. This issue will be addressed in a future full account.
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19. 3 (see Supporting Information for details). Authentic samples of 3 were no longer available.