Transformation of the B Ring to the C Ring of Bryostatins by Csp 3 -H Amination and Z to E Isomerization

An interesting approach to transform the B ring of bryostatins to the C ring has been developed. The key tactics of the approach feature an intramolecular Csp -H bond amination to form spirocyclic hemiaminal, which undergoes ring opening to afford the C ring found in bryostatin 17. The subsequent ep...

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Bibliographic Details
Published inOrganic letters Vol. 19; no. 19; pp. 5232 - 5235
Main Authors Lu, Ji, Zhang, Yuebao, Yang, WenYu, Guo, Qianyou, Gao, Lu, Song, Zhenlei
Format Journal Article
LanguageEnglish
Published United States 06.10.2017
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Summary:An interesting approach to transform the B ring of bryostatins to the C ring has been developed. The key tactics of the approach feature an intramolecular Csp -H bond amination to form spirocyclic hemiaminal, which undergoes ring opening to afford the C ring found in bryostatin 17. The subsequent epoxidation/oxidation sequence results in Z to E isomerization of the exo-cyclic enoate, delivering the common precursor, which could be transformed into the C ring found in bryostatins 1, 2, 4-9, 12, 14, and 15.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.7b02510