Applications of crotyldiisopinocampheylboranes in synthesis: a formal total synthesis of (+)-calyculin A
Canadian Journal of Chemistry2001Vol. 79(11), pp. 1562–1592
Citations Over TimeTop 21% of 2001 papers
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
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 CornforthMeyers approach to the synthesis of the oxazole fragment.Key words: calyculin, marine natural product, phosphatase inhibitor, total synthesis, palladium catalyzed coupling reactions, allylboration reactions, aldol reactions, spiroketal, CornforthMeyers oxazole reaction.
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