A Double Iodoetherification of σ-Symmetric Diene Acetals for Installing Four Stereogenic Centers in a Single Operation: Short Asymmetric Total Synthesis of Rubrenolide

✍ Scribed by Hiromichi Fujioka; Yusuke Ohba; Hideki Hirose; Kenichi Murai; Yasuyuki Kita

• Publisher: John Wiley and Sons
• Year: 2005
• Tongue: English
• Weight: 127 KB
• Volume: 117
• Category: Article
• ISSN: 0044-8249
• DOI: 10.1002/ange.200461584

✦ Synopsis

Many biologically active natural products contain multiple chiral centers and occur in their optically active form, and therefore the development of methodologies that can lead to multiple chiral centers is desirable in synthetic organic chemistry. Recently, we developed the intramolecular haloetherification of chiral ene acetals from (R,R)-hydrobenzoin in which two new chiral centers are formed at remote positions. [1] As an extension of this remote asymmetric induction method we studied the reaction of acyclic s-symmetric diene acetals, and found an unprecedented double intramolecular haloetherification leading to the formation of four asymmetric centers in a single operation (Scheme 1).