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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Published in | Organic letters Vol. 19; no. 19; pp. 5232 - 5235 |
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Main Authors | , , , , , |
Format | Journal Article |
Language | English |
Published |
WASHINGTON
Amer Chemical Soc
06.10.2017
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Subjects | |
Online Access | Get full text |
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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. |
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ISSN: | 1523-7060 1523-7052 |
DOI: | 10.1021/acs.orglett.7b02510 |