Total synthesis of (+)-spirastrellolide A methyl ester: Challenges and discoveries
2013 ◽
Vol 85
(6)
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pp. 1133-1147
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Keyword(s):
This review focuses on recent synthetic efforts by our group towards spirastrellolide A methyl ester, a complex marine macrolide containing two spiroacetal ring systems that shows promising anticancer properties. The evolution of a flexible, modular strategy leading to the first total synthesis of (+)-spirastrellolide A methyl ester, and the associated challenges overcome, are highlighted, particularly in dealing with the initial structural ambiguities. This work enabled the development of an improved second-generation synthesis, which revealed a critical dependence of the key macrolactonization step on the nature of the protecting groups in the linker region between the spiroacetal motifs.
2012 ◽
Vol 51
(11)
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pp. 2749-2753
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2013 ◽
Vol 19
(11)
◽
pp. 3596-3608
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2012 ◽
Vol 10
(30)
◽
pp. 5861
◽
2011 ◽
Vol 50
(37)
◽
pp. 8739-8744
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2008 ◽
Vol 47
(16)
◽
pp. 3021-3025
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