Asymmetric synthesis of a tricyclic benzofuran motif: a privileged core structure in biologically active molecules
文献信息
发布日期
2010-09-08
DOI
10.1039/C0OB00331J
影响因子
3.876
作者
Henrik Sundén
查看原文
摘要
An efficient synthetic strategy for the asymmetric synthesis of a hexahydrodibenzofuran core structure, with a quaternary stereogenic center, emerges by employing a chiral reduction using Corey's (S)-Me-CBS-oxazaborolidine reagent followed by a Mitsunobu reaction to set the stereochemistry. A Pd-mediated intramolecular Heck reaction concludes the tricyclic core structure. Finally, a Pd/C catalyzed reduction yields the target molecule in 21% overall yield over 6 steps.
期刊推荐
Journal of Organometallic Chemistry
Journal of Medicinal Chemistry
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Proceedings of the National Academy of Sciences of the United States of America
Fibre Chemistry
Russian Chemical Reviews
Planta Medica
Organic Preparations and Procedures International
European Journal of Wood and Wood Products
Helvetica Chimica Acta
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来源期刊
Organic & Biomolecular Chemistry
CiteScore:
3.4
自引率:
10.3%
年发文量:
1041
Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.
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