Total Synthesis of Montiporyne E

Author

Jian Chen

Abstract

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

Publication Date

2005

Document Type

Thesis

Student Type

Graduate

Degree Name

Chemistry (MS)

Department, Program, or Center

School of Chemistry and Materials Science (COS)

Advisor

Christina Collison

Comments

Physical copy available from RIT's Wallace Library at QD305.H8 C44 2005

Recommended Citation

Chen, Jian, "Total Synthesis of Montiporyne E" (2005). Thesis. Rochester Institute of Technology. Accessed from
https://repository.rit.edu/theses/8271

Campus

RIT – Main Campus