Rhodium-Catalyzed [4+3] Cycloaddition to Furans: Direct Access to Functionalized Bicyclo[5.3.0]decane Derivatives

• Published in: European journal of organic chemistry Vol. 2016; no. 1; pp. 41 - 44
• Main Authors: Krainz, Tanja, Chow, Sharon, Korica, Natasa, Bernhardt, Paul V., Boyle, Glen M., Parsons, Peter G., Davies, Huw M. L., Williams, Craig M.
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 01.01.2016; WILEY‐VCH Verlag; Wiley; Wiley Subscription Services, Inc
• Subjects: Antitumor agents; Chemistry; Chemistry, Organic; Cycloaddition; Furans; Homogeneous catalysis; Kinases; Physical Sciences; Rhodium; Science & Technology; ORGANIC-SYNTHESIS; INGENOL; PROTEIN-KINASE-C; ASYMMETRIC-SYNTHESIS; VINYLCARBENOIDS; NATURAL-PRODUCTS; STRATEGY; THAPSIGARGINS; Cycloaddition; Antitumor agents; Rhodium; Homogeneous catalysis; 7-MEMBERED RINGS; Furans; CYCLOPROPANATION COPE REARRANGEMENT
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.201501271

An efficient method to directly access the bicyclo[5.3.0]decane core was achieved by rhodium‐catalyzed reaction of a novel donor–acceptor cyclopentenyl diazocarboxylate with a variety of furans. As this motif is commonly found within bioactive antitumor natural products, selected systems were further manipulated and evaluated against cancer cell lines sensitive to protein kinase C (PKC) activation. A cyclic donor–acceptor diazo compound was synthesized for the first time, facilitating direct access to the bicyclo[5.3.0]decane motif, which is commonly seen in a number of prominent natural products active against cancer. Some examples were evaluated against various PKC cancer cell lines.