Stereospecific Construction of Contiguous Quaternary and Tertiary Stereocenters by Rearrangement from Indoline-2-methanol to 2,2,3-Trisubstituted Tetrahydroquinoline: Application to an Efficient Total Synthesis of Natural Virantmycin

✍ Scribed by Mayuko Ori; Narihiro Toda; Kazuko Takami; Keiko Tago; Hiroshi Kogen

• Publisher: John Wiley and Sons
• Year: 2003
• Tongue: English
• Weight: 124 KB
• Volume: 42
• Category: Article
• ISSN: 0044-8249
• DOI: 10.1002/anie.200351069

✦ Synopsis

The stereoselective construction of chiral quaternary stereocenters is one of the most challenging problems in synthetic organic chemistry. [1] Substituted tetrahydroquinolines and tetrahydroisoquinolines have attracted considerable attention from organic and medicinal chemists, primarily because they display a wide range of physiological activities. [1c, 2] These ring systems are present in various important natural products. [2] Moreover, chiral quaternary centers are often essential for these compounds. For example, chiral contiguous quaternary and tertiary stereocenters are found in virantmycin (6 a), [3] a potent antiviral agent (Scheme 1). Recently, Shibasaki et al. reported an elegant synthesis of 1,1-disubstituted tetrahy-