Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 140, Issue 38, Pages 12120-12136Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.8b06955
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Funding
- Cancer Prevention Research Institute of Texas (CPRIT)
- Welch Foundation [C-1819]
- AbbVie Stemcentrx
- Rice University
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Shishijimicin A is a scarce marine natural product with highly potent cytotoxicities, making it a potential payload or a lead compound for designed antibody drug conjugates. Herein, we describe an improved total synthesis of shishijimicin A and the design, synthesis, and biological evaluation of a series of analogues. Equipped with appropriate functionalities for linker attachment, a number of these analogues exhibited extremely potent cytotoxicities for the intended purposes. The synthetic strategies and tactics developed and employed in these studies included improved preparation of previously known and new sulfenylating reagents such as PhthNSSMe and related compounds.
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