Total synthesis of cyercene A and the biomimetic synthesis of (+/-)-9,10-deoxytridachione and (+/-)-ocellapyrone A

Rodriguez, R., Adlington, R. M., Eade, S. J., Walter, M. W., Baldwin, J. E., Moses, J. E. (May 2007) Total synthesis of cyercene A and the biomimetic synthesis of (+/-)-9,10-deoxytridachione and (+/-)-ocellapyrone A. Tetrahedron, 63 (21). pp. 4500-4509. ISSN 0040-4020

DOI: 10.1016/j.tet.2007.03.057


This paper summarises our detailed study towards the biomimetic synthesis of the complex polypropionate derived natural product (+/-)-9,10-deoxytridachione. A previous study based on the elaboration of functionalised gamma-pyrones allowed us to synthesise cyercene A. The same efficient methodology has been applied for the elaboration of a more complex fully conjugated gamma-pyrone polyene. Our approach centred on a key tandem Suzuki-coupling/electrocyclisation reaction, which supports a possible biosynthetic pathway for this class of natural products. A related compound was obtained during our studies, which we identified as the correct structure of ocellapyrone A. (C) 2007 Published by Elsevier Ltd.

Item Type: Paper
Additional Information: Tetrahedron
Uncontrolled Keywords: total synthesis natural products electrocyclisation reaction cascade methide intermediate generation streptomyces-spectabilis polypropionate pyrones efficient method marine mollusks metabolites snf4435c biosynthesis propionate spectinabilin Chemistry
CSHL Authors:
Depositing User: Matthew Dunn
Date: 21 May 2007
Date Deposited: 17 Nov 2020 21:32
Last Modified: 17 Nov 2020 21:32

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