Applications of crotyldiisopinocampheylboranes in synthesis: a formal total synthesis of (+)-calyculin A
2001 ◽
Vol 79
(11)
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pp. 1562-1592
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Keyword(s):
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.
2017 ◽
Vol 15
(44)
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pp. 9408-9414
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Keyword(s):
2017 ◽
Vol 23
(52)
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pp. 12714-12717
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2005 ◽
Vol 9
(1)
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pp. 113-120
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Keyword(s):
2000 ◽
Vol 72
(9)
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pp. 1783-1786
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