AI Article Synopsis
- A ring-closing alkene metathesis and oxyselenation sequence was developed for the synthesis of sodium salts of proposed structures related to the cytotoxin aruncin B and its regioisomer, but free acids were unattainable.
- Detailed spectroscopic analysis revealed that the original structure of aruncin B needed significant revision, leading to the identification of it as a Z-γ-alkylidenebutenolide.
- A new synthesis method combining a β-iodo Morita-Baylis-Hillman reaction with Sonogashira cross-coupling was used to create aruncin B and 14 analogues for biological testing due to its efficiency and versatility.
Article Abstract
A ring-closing alkene metathesis (RCM)/ oxyselenation-selenoxide elimination sequence was established to the sodium salts E- and Z-25 of the originally proposed structure for the recently isolated cytotoxin aruncin B (1), as well as to the sodium salt Z-34 of a related ethyl ether regioisomer; however, none of their corresponding free acids could be obtained. Their acid sensitivity, together with detailed analysis of the spectroscopic data indicated that profound structural revision was necessary. This led to reassignment of aruncin B as a Z-γ-alkylidenebutenolide Z-36. Although a related RCM/ oxyselenation-selenoxide elimination sequence was used to confirm the γ-alkylidenebutenolide motif, a β-iodo Morita-Baylis-Hillman reaction/ Sonogashira cross-coupling-5-exo-dig lactonisation sequence was subsequently developed, due to its brevity and flexibility for diversification. Aruncin B (36), together with 14 γ-alkylidenebutenolide analogues, were generated for biological evaluation.
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|---|---|
| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC5725683 | PMC |
| http://dx.doi.org/10.1002/chem.201702949 | DOI Listing |
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