Loading...
Synthesis of the AB ring system of clifednamide utilizing Claisen rearrangement and Diels-Alder reaction as key steps.
Loke, Inga Bentzinger, Guillaume Holz, Julia Raja, Aruna Bhasin, Aman Sasse, Florenz Köhn, Andreas Schobert, Rainer Laschat, Sabine
Loke, Inga
Bentzinger, Guillaume
Holz, Julia
Raja, Aruna
Bhasin, Aman
Sasse, Florenz
Köhn, Andreas
Schobert, Rainer
Laschat, Sabine
Citations
Altmetric:
Advisors
Editors
Other Contributors
Issue Date
2016-01-21
Submitted date
Files
Loading...
Open Access article
Adobe PDF, 487.91 KB
Other Titles
Abstract
In order to construct the functionalized AB ring system of clifednamide, member of the class of macrocyclic tetramic acid lactams, a synthesis was developed which utilized an Ireland-Claisen rearrangement and an intramolecular Diels-Alder reaction. Starting from di-O-isopropylidene-d-mannitol the allyl carboxylate precursor for the sigmatropic rearrangement was prepared. This rearrangement proceeded diastereoselectively only in the presence of an allyl silyl ether instead of the parent enone in the side chain, as suggested by deuteration experiments. A subsequent Diels-Alder reaction yielded the target ethyl hexahydro-1H-indene-carboxylate with high diastereoselectivity. Quantum-chemical investigations of this intramolecular Diels-Alder reaction support the proposed configuration of the final product.
Citation
Synthesis of the AB ring system of clifednamide utilizing Claisen rearrangement and Diels-Alder reaction as key steps. 2016, 14 (3):884-94 Org. Biomol. Chem.
Publisher
Journal
PubMed ID
PubMed Central ID
Additional Links
Embedded video
Type
Article
Language
en
Description
Series/Report no.
ISSN
1477-0539