Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 130, Issue 21, Pages 6660-+Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja8022169
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Funding
- Intramural NIH HHS Funding Source: Medline
- NIGMS NIH HHS [R01 GM028961-25A1, R01 GM028961-21, R01 GM028961-19, R01 GM028961, R01 GM028961-18, R01 GM028961-20, R01 GM028961-22, R01 GM028961-26, R01 GM028961-24, R01 GM028961-23, GM28961] Funding Source: Medline
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Highly potent bryostatin analogues which contain the complete bryostatin core structure have been synthesized using a pyran annulation approach as a key strategic element. The A ring pyran was assembled using a pyran annulation reaction between a C(1)-C(8) hydroxy allylsilane and an aldehyde comprising C(9)-C(13). This pyran was transformed to a new hydroxy allyisilane and then coupled with a preformed C ring aldehyde subunit in a second pyran annulation, with concomitant formation of the B ring. This tricyclic intermediate was elaborated to bryostatin analogues which displayed nanomolar to subnanomolar affinity for PKC, but displayed properties indistinguishable from a phorbol ester in a proliferation/attachment assay.
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