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(3)-H bond amination to form spirocyclic hemiaminal, which undergoes ring opening to afford the C ring found in bryostatin 17. The subsequent...

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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 WASHINGTON Amer Chemical Soc 06.10.2017
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ANTITUMOR MACROLIDES
PROTEIN-KINASE-C
BOND-FORMING HYDROGENATION
ANALOGS
IN-VIVO
ANTINEOPLASTIC AGENTS
LEUKEMIA-CELLS
DIFFERENTIATION
PHORBOL ESTER
DERIVATIVES
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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(3)-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