Cycloadditions in the Total Synthesis of Sporolide B

✍ Scribed by Pengfei Li; Dirk Menche

• Publisher: John Wiley and Sons
• Year: 2009
• Tongue: English
• Weight: 272 KB
• Volume: 48
• Category: Article
• ISSN: 0044-8249
• DOI: 10.1002/anie.200901894

✦ Synopsis

Abstract

Closing rings: A recent total synthesis of sporolide B by the Nicolaou group is highlighted by two advantageous cycloadditions. Firstly, a regioselective [2+2+2] cycloaddition of highly elaborate substrates assembles the halogenated aromatic ring and subsequently an ortho‐quinone [4+2] cyclization closes stereoselectively the dioxane‐containing macrocycle. These approaches should be considered in complex target syntheses.magnified image