First total synthesis of (±)-methyl gummiferolate using a homoallyl-homoallyl radical rearrangement reaction

Organic Letters

Volumn 1, Issue 10, 1999, Pages 1627-1629

  Toyota, Masahiro ^a   Yokota, Masahiro ^a   Ihara, Masataka ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001478546     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990264u     Document Type: Article

References (14)

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9. 2 (1.20 L), and then silica gel (300 g) was added. After vigorous stirring for 2 days, the mixture was filtered through Celite. The filtrate was concentrated to give an oil, which was chromatographed on silica gel. Elution with hexane followed by a 3:1 mixture of hexanes-EtOAc successively afforded the bicyclo[3.2.1]octane compound 10 (21.4 g, 50%) and 9, containing a small amount of tin species. After washing of the crude 9 with hexane, the bicyclo[2.2.2]octane compound 9 (6.38 g, 32%), mp 67-69°C, was isolated.
10. 120Sn 542.2785, found 542.2799.
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