Organic Letters
Organic Letters
5 years ago

Transformation of the B Ring to the C Ring of Bryostatins by Csp3–H Amination and Z to E Isomerization

Transformation of the B Ring to the C Ring of Bryostatins by Csp3–H Amination and Z to E Isomerization
Zhenlei Song, Yuebao Zhang, WenYu Yang, Lu Gao, Qianyou Guo, Ji Lu
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 Csp3–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.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b02510

DOI: 10.1021/acs.orglett.7b02510

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