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Monday, June 25, 2012
Douglass F. Taber
University of Delaware

Substituted Benzenes: The Reddy Synthesis of Isofregenedadiol

Jianbo Wang of Peking University (Org. Lett. 2011, 13, 4988. ) and Patrick Y. Toullec and Véronique Michelet of Chimie ParisTech (Org. Lett. 2011, 13, 6086. ) developed conditions for the electrophilic acetoxylation of a benzene derivative 1. Seung Hwan Cho and Sukbok Chang of KAIST (J. Am. Chem. Soc. 2011, 133, 16382. ) and Brenton DeBoef of the University of Rhode Island (J. Am. Chem. Soc. 2011, 133, 19960. ) devised protocols for the electrophilic imidation of a benzene derivative 3.

Vladimir V. Grushin of ICIQ Tarragona optimized (J. Am. Chem. Soc. 2011, 133, 10999. ) the cyanation of a bromobenzene 6 to the nitrile 7. Hua-Jian Xu of the Hefei University of Technology (J. Org. Chem. 2011, 76, 8036. ) and Myung-Jong Jin of Inha University (Org. Lett. 2011, 13, 5540. ) established conditions for the efficient Heck coupling of a chlorobenzene 8.

Jacqueline E. Milne of Amgen/Thousand Oaks reduced (J. Org. Chem. 2011, 76, 9519. ) the adduct from the addition of 11 to 12 to deliver the phenylacetic acid 13. Jeffrey W. Bode of ETH Zurich effected (Angew. Chem. Int. Ed. 2011, 50, 10913. ) Friedel-Crafts alkylation of 14 with the hydroxamate 15 to give the meta product 16.

B. V. Subba Reddy of the Indian Institute of Chemical Technology, Hyderabad took advantage (Tetrahedron Lett. 2011, 52, 5926. ) of the directing ability of the amide to effect selective ortho acetoxylation of 17. Similarly, Frederic Fabis of the Université de Caen Basse-Normandie used (J. Org. Chem. 2011, 76, 6414. ) the methoxime of 19 to direct ortho bromination, leading to 20.

Teck-Peng Loh of Nanyang Technological University showed (Chem. Commun. 2011, 47, 10458. ) that the carbamate of 21 directed ortho C-H functionalization, to give the ester 23. Yoichiro Kuninobu and Kazuhiko Takai of Okayama University rearranged (Chem. Commun. 2011, 47, 10791. ) the allyl ester 24 directly to the ortho-allylated acid 25.

Youhong Hu of the Shanghai Institute of Materia Medica (J. Org. Chem. 2011, 76, 8495. ) and Graham J. Bodwell of Memorial University (J. Org. Chem. 2011, 76, 9015. ) condensed a chromene 26 with a nucleophile 27 to give the arene 28. C. V. Ramana of the National Chemical Laboratory prepared (Tetrahedron Lett. 2011, 52, 4627. ) the arene 31 by condensing 29 with 30. En route to Isofregenedadiol 36, D. Srinivasa Reddy, now also at the National Chemical Laboratory, devised (Org. Lett. 2011, 13, 3690. ) a one-pot, four-step sequence to prepare the arene 35.

D. F. Taber, Org. Chem. Highlights 2012, June 25.
URL: https://www.organic-chemistry.org/Highlights/2012/25June.shtm