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First synthesis of mastigophorenes A and B, by biomimetic oxidative coupling of herbertenediol

Bringmann, G., Pabst, T., Rycroft, D.S., and Connolly, J.D. (1999) First synthesis of mastigophorenes A and B, by biomimetic oxidative coupling of herbertenediol. Tetrahedron Letters, 40 (3). pp. 483-486. ISSN 0040-4039 (doi:10.1016/S0040-4039(98)02487-3)

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Publisher's URL: http://dx.doi.org/10.1016/S0040-4039(98)02487-3

Abstract

The first synthesis of mastigophorenes A and B by oxidative phenolic coupling of partially protected derivatives of their joint natural monomeric half, herbertenediol, is described. The synthesis starts from this diol itself or from the corresponding aldehyde, both available by isolation from the liverwort, Herbertus aduncus. After transformation of herbertenediol to a chemically appropriate monophenolic coupling precursor, the oxidative dehydrodimerization was brought about using (tert-BuO)2, followed by deprotection to give mastigophorenes A and B in their 'natural' atropisomeric ratio, as isolated from the liverwort.

Item Type:Article
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Connolly, Prof Joseph and Rycroft, Dr David
Authors: Bringmann, G., Pabst, T., Rycroft, D.S., and Connolly, J.D.
Subjects:Q Science > QD Chemistry
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Tetrahedron Letters
ISSN:0040-4039

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