Montiporyne A-F is a family of new diacetylenic natural products recently isolated from stony coral Montipora sp. Biological study shows that these compounds exhibit bioactivity against certain solid tumor cells. Of particular interest is Montiporyne E, whose molecular structure is comprised of an interesting seven-membered lactam ring and a diacetylenic sidechain, which is a common structural feature among the Montiporyne family members.
An efficient synthesis of Montiporyne E is described in this paper. The seven-membered lactam ring was constructed using a Beckmann rearrangement. The desired natural product was synthesized using a Sonograshira coupling of the seven-membered lactam vinyl triflate with a mono-substituted diyne side chain.
The structure of the natural product Montiporyne E was confirmed by X-ray crystallographic analysis, mass spectrometry, FT-IR, and NMR spectroscopy including 1H-NMR, 13C-NMR, 1H-1H COSY, 13C-DEPT, HMQC, HMBC. All spectral data were in agreement with its reported structure.
Library of Congress Subject Headings
Acetylene--Synthesis; Antineoplastic agents--Synthesis
Department, Program, or Center
School of Chemistry and Materials Science (COS)
Chen, Jian, "Total Synthesis of Montiporyne E" (2005). Thesis. Rochester Institute of Technology. Accessed from
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