Applications of crotyldiisopinocampheylboranes in synthesis: A formal total synthesis of (+)-calyculin A

Oren P. Anderson, Anthony G.M. Barrett, Jeremy J. Edmunds, Shun Ichiro Hachiya, James A. Hendrix, Kiyoshi Horita, James W. Malecha, Christopher J. Parkinson, Andrew Vansickle

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Abstract

The formal total synthesis of the marine metabolite (+)-calyculin A is reported. The key steps involve (i) the use of Brown allylboration chemistry to control the relative and absolute stereochemistry of homoallylic alcohol arrays, thus setting eight of the desired stereocenters; (ii) Stille coupling methodology in the construction of the cyano tetraene unit of the natural product; and (iii) a modified Cornforth-Meyers approach to the synthesis of the oxazole fragment.

Original languageEnglish
Pages (from-to)1562-1592
Number of pages31
JournalCanadian Journal of Chemistry
Volume79
Issue number11
DOIs
Publication statusPublished - 2001

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    Anderson, O. P., Barrett, A. G. M., Edmunds, J. J., Hachiya, S. I., Hendrix, J. A., Horita, K., Malecha, J. W., Parkinson, C. J., & Vansickle, A. (2001). Applications of crotyldiisopinocampheylboranes in synthesis: A formal total synthesis of (+)-calyculin A. Canadian Journal of Chemistry, 79(11), 1562-1592. https://doi.org/10.1139/cjc-79-11-1562