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(+)-Dimericbiscognienyne A: Total Synthesis and Mechanistic Investigations of the Key Heterodimerization

Author:
Kim, Geon, Kim, Myungjo J., Chung, Garam, Lee, Hee-Yoon, Han, Sunkyu
Source:
Organic letters 2018 v.20 no.21 pp. 6886-6890
ISSN:
1523-7052
Subject:
cycloaddition reactions, diastereomers, dimerization, organic compounds
Abstract:
The first total synthesis of (+)-dimericbiscognienyne A is described. Key to the successful access to (+)-dimericbiscognienyne A was a biosynthetically inspired Diels–Alder reaction between two differential epoxyquinoid monomers and the subsequent intramolecular hemiacetal formation. The selective formation of the natural product among other possible diastereomers during the late-stage [4+2] cycloaddition reaction was investigated by DFT calculations and experimental control studies.
Agid:
6194686