Antimicrobial algal metabolites of unusual structure. Concise synthesis of the highly oxygenated [4.4]Spirononene dimethyl gloiosiphone a by ring expansion of dimethyl squarate

Tetrahedron

Volumn 53, Issue 26, 1997, Pages 8913-8926

  Sturino, Claudio F ^a,b   Doussot, Pascale ^a   Paquette, Leo A ^a  

^a OHIO STATE UNIVERSITY   (United States)

^b Allelix Biopharmaceuticals ^*  (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

DIMETHYLGLOIOSIPHONE A; UNCLASSIFIED DRUG;

ANTIMICROBIAL ACTIVITY; ARTICLE; CATALYSIS; CHROMATOGRAPHY; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; OXIDATION; PRIORITY JOURNAL; RACEMIC MIXTURE;

ALGAE;

EID: 0030753762     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)90400-2     Document Type: Article

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76. The oxidation of methyl enol ethers with DDQ in methanol at 0 °C (Paquette, L. A.; Poupart, M.-A. J. Org. Chem. 1993, 58, 4245) and of triisopropylsilyl enol ethers with CAN (Evans, P. A.; Longmire, J. M.; Modi, D. P. Tetrahedron Lett. 1995, 36, 3985) has previously been described.
77. The oxidation of methyl enol ethers with DDQ in methanol at 0 °C (Paquette, L. A.; Poupart, M.-A. J. Org. Chem. 1993, 58, 4245) and of triisopropylsilyl enol ethers with CAN (Evans, P. A.; Longmire, J. M.; Modi, D. P. Tetrahedron Lett. 1995, 36, 3985) has previously been described.
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85. Provided by Prof. W. C. Still. The illustrations were generated with CHEM-3D PLUS (Cambridge Scientific Co., Inc., Cambridge, MA, 1990).