Synthesis of a New 2,3-Diaminoconduritol with Conduritol F Structure

Date

2012-09-01

Author

Ekmekci, Zeynep
Balcı, Metin

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A new 2,3-diaminoconduritol derivative with the conduritol F structure was prepared starting from cyclohexa-1,4-diene. Initially, a lactam, prepared by the cycloaddition of chlorosulfonyl isocyanate (CSI) to cyclohexa-1,4-diene, was converted into an amino acid. The conversion of the acid functionality into an isocyanate resulted in the formation of an imidazolidinone derivative, formed by an intramolecular cyclization. In the second part of this work, the known anhydride, 3a,4,7,7a-tetrahydroisobenzofuran-1,3-dione was successfully converted into the desired bis(carbamate). The bromination of the double bond in the six-membered ring followed by a DBU-induced (DBU = 1,8-diazabicyclo[5.4.0]undec-7-ene) HBr elimination furnished the symmetrical diene. The photooxygenation of the diene unit afforded the bicyclic endoperoxide. The reaction of the endoperoxide with thiourea followed by acetylation resulted in the formation of a syn-configured diacetate. The deprotection of the urethane and acetate groups gave the new 2,3-diaminoconduritol with the conduritol F structure.

Subject Keywords

Natural products , Total synthesis, Configuration determination, Rearrangement, Oxygenation

URI

https://hdl.handle.net/11511/57493

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

DOI

https://doi.org/10.1002/ejoc.201200582

Collections

Graduate School of Natural and Applied Sciences, Article

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Citation Formats

Z. Ekmekci and M. Balcı, “Synthesis of a New 2,3-Diaminoconduritol with Conduritol F Structure,” EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, pp. 4988–4995, 2012, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/57493.