e-Publications@Marquette

Title

Spectral Data for "Generation of Molecular Complexity from Cyclooctatetraene: Preparation of Optically Active Protected Aminocycloheptitols and Bicyclo[4.4.1]undecatriene"

Authors

Mohamed F. El-Mansy, Marquette University
Anobick Sar, Marquette University
Sergey V. Lindeman, Marquette UniversityFollow
William A. Donaldson, Marquette UniversityFollow

Grant Title

Natural Products Synthesis via Organoiron Methodology

Document Type

Spectral Data

Format Type

.pdf

Publication Date

2-2013

Abstract

Spectral data created in the course of the research project. Supports specific findings in "Generation of Molecular Complexity from Cyclooctatetraene: Preparation of Optically Active Protected Aminocycloheptitols and Bicyclo[4.4.1]undecatriene".

The racemic (6-cyclo-heptadienyl)Fe(CO)₃⁺ cation ((±)-7), prepared from cyclooctatetraene, was treated with a variety of carbon and heteroatom nucleophiles. Attack took place at the less hindered C¹ dienyl carbon and decomplexation of the (cycloheptadiene)Fe(CO)₃ complexes gave products rich in functionality for further synthetic manipulation. In particular, a seven-step route was developed from racemic (6-styryl-2,4-cycloheptadien-1-yl)phthalimide ((±)-9 d) to afford the optically active aminocycloheptitols (−)-20 and (+)-20.

Recommended Citation

El-Mansy, Mohamed F.; Sar, Anobick; Lindeman, Sergey V.; and Donaldson, William A., "Spectral Data for "Generation of Molecular Complexity from Cyclooctatetraene: Preparation of Optically Active Protected Aminocycloheptitols and Bicyclo[4.4.1]undecatriene"" (2013). Natural Products Synthesis via Organoiron Methodology. 8.
https://epublications.marquette.edu/data_nps/8