## Abstract The absolute configurations of acetylated bretonin A (= (+}‐(R)‐__1‐[(acetoxy)methyl]‐2__‐{[(4E,__6__E,__8__E)‐__dodeca__‐4,6,8‐__trienyl__]__oxy__}__ethyl__ 4‐__acetoxybenzoate__; (−)‐1b) and isobretonin A (= (+)‐(S)‐3‐{[(__4__E,__6__E,__8__E)‐__do‐deca‐4,6,8‐trienyl]oxy}‐2‐hydroxyprop
The Structure and Configuration of Novel Polycyclic Products Derived from an Alicyclic 1,5,9-Trione and Binucleophiles
✍ Scribed by Natalia S. Kravchenko; Vladimir A. Denisenko; Taisia I. Akimova
- Publisher
- John Wiley and Sons
- Year
- 2009
- Tongue
- German
- Weight
- 174 KB
- Volume
- 92
- Category
- Article
- ISSN
- 0018-019X
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✦ Synopsis
Abstract
As a continuation of our research of reactions with alicyclic 1,5,9‐trione 1 and its polycyclic form 2, we have studied their reactions with binucleophiles, e.g., phenylene‐1,2‐diamine and 2‐aminophenol, leading to novel N,O‐containing polycyclic compounds. Trione 1 formed double cyclization products 11 and 12 with 2‐aminophenol and triple cyclization product 15 with phenylene‐1,2‐diamine. Hemiacetal 2 and its dehydration product 5 reacted with binucleophiles through initial isomerization into the intermediate cyclic form 4 of trione 1. Thus, ketone 5 reacted with 2‐aminophenol stereoselectively unlike the hemiacetal 2. The structure and configuration of the reaction products were studied by using advanced spectroscopic techniques including 1D‐ and 2D‐NMR experiments.
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