Site selective oxidation of tricyclo[3.3.1.13,7]decane (adamantane) and some of its derivatives using fungi of the genus Absidia

Colin H. Ridyard, Roger A. Whittaker, Stanley D. Higgins, Stanley M. Roberts, Andrew J. Willets, Patrick D. Bailey, Georgina M. Rosair

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

Tricyclo[3.3.1.13,7]decane la has been converted into 1-hydroxytricyclo[3.3.1.13,7]decane 1b, tricyclo[3.3.1.1 3,7]decane-1,4ax-diol 4b, tricyclo[3.3.1.13,7]decane-1,3- diol 3b and to a lesser extent, 2-hydroxytricyclo[3.3.1.13,7]decane 4a (20 to 40% overall yield) using the microorganisms Absidia glauca (IMI 239693), A. cylindrospora (IMI 342950), A. spinosa (IMI 193887), A. spinosa var. biappendiculata (IMI 238610) and A. cylindrospora var. nigra (IMI 240053) as biocatalysts: In addition, A. cylindrospora (IMI 342950) converted tricyclo[3.3.1.13,7]decane-1-carboxylic acid 1c into 4ax-hydroxytricyclo[3.3.1.13,7]decane-1-carboxylic acid 4c with almost complete regioselectivity. Tricyclo[3.3.1.13,7]decane derivatives 1d-g were used as biohydroxylation substrates with A. cylindrospora (IMI 342950), giving selective biohydroxylation at the 4ax- and/or the 3-position. The 4ax-selectivity was confirmed by X-ray crystal structure determinations of 4b, 4c and 4j.

Original languageEnglish
Pages (from-to)1811-1819
Number of pages9
JournalJournal of the Chemical Society, Perkin Transactions 2
Volume9
DOIs
Publication statusPublished - Sep 1996

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