New Synthetic Technology for the Rapid Construction of Novel Heterocycles—Part 1: The Reaction of Dess – Martin Periodinane with Anilides and Related Compounds

✍ Scribed by K. C. Nicolaou; Yong-Li Zhong; Phil S. Baran

• Publisher: John Wiley and Sons
• Year: 2000
• Tongue: English
• Weight: 114 KB
• Volume: 112
• Category: Article
• ISSN: 0044-8249
• DOI: 10.1002/(sici)1521-3757(20000204)112:3<636::aid-ange636>3.0.co;2-f

✦ Synopsis

Contemporary organic synthesis is faced with the challenge of developing simple methods for the rapid construction of complex, biologically relevant compounds which rival the complexity and diversity of natural products for combinatorial chemistry, biological screening, and chemical biology studies. Total synthesis endeavors provide novel forums and opportunities for exploration and for the discovery and development of new chemistry to address this formidable task. During the course of our recent total synthesis of the CP molecules [1] we observed the unexpected conversion of 1 into 2 (Scheme 1), brought about by exposure of 1 to DMP [2] in OH O O TBSO O O O OH O O TBSO O O O O N O H DMP O H N benzene, ∆ 1 2 (48%) Scheme 1. Serendipitous observation leading to the present methodologies. DMP Dess ± Martin periodinane, TBS tert-butyldimethylsilyl.

refluxing benzene. This serendipitous discovery directly led to the development of a number of new chemical processes for the construction of molecular diversity, while unearthing a new paradigm for periodinane-mediated reactions with ani-