Stereoselective Synthesis of the Functionalized C2–C10 Fragment of Clavulactone

✍ Scribed by Zuozhong ZHOU; Dong SUO; Zhenyu YANG; Lin CHEN; Taishan HU; Zhujun YAO

• Publisher: John Wiley and Sons
• Year: 2009
• Tongue: English
• Weight: 110 KB
• Volume: 27
• Category: Article
• ISSN: 0256-7660
• DOI: 10.1002/cjoc.200990006

✦ Synopsis

A stereoselective synthesis of all functionalized C2-C10 fragment 13 of the antitumor marine natural product clavulactone was accomplished, starting from the commercially available 3-methylglutaric acid anhydride. Desymmetrization of 3-methylglutaric acid anhydride with (S)-α-phenylethanamine was successfully employed as a key step to embed the isolated C8-methyl group with the correct absolute configuration (99% de). The C3-C4 cis-double bond was stereospecifically furnished by an RCM (ring-closing metathesis) approach. Fragment 13 contains all preset functionalities and will be a useful precursor for the convergent total synthesis of clavulactone.