Stereoselective Synthesis of the Cytotoxic 14-Membered Macrolide Aspergillide A
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comunitat-uji-handle2:10234/7053
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http://dx.doi.org/10.1021/jo9027038 |
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Title
Stereoselective Synthesis of the Cytotoxic 14-Membered Macrolide Aspergillide AAuthor (s)
Date
2010Publisher
American Chemical SocietyISSN
0022-3263Bibliographic citation
Journal of Organic Chemistry ( 2010) 75, 5, p. 1775–1778Type
info:eu-repo/semantics/articlePublisher version
http://pubs.acs.org/doi/abs/10.1021%2Fjo9027038Abstract
A stereoselective synthesis of the cytotoxic 14-membered macrolide aspergillide A has been performed. The preparation of a cis-2,6-disubstituted tetrahydropyran ring via stereoselective reduction of an intermediate ... [+]
A stereoselective synthesis of the cytotoxic 14-membered macrolide aspergillide A has been performed. The preparation of a cis-2,6-disubstituted tetrahydropyran ring via stereoselective reduction of an intermediate cyclic hemiacetal was one key feature of the synthesis. The macrocyclic lactone ring was created by means of a ring-closing metathesis (RCM), whereby the new C═C bond displayed exclusively the undesired Z configuration. Conversion to the required E configuration was achieved via photochemical isomerization. [-]
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