Progress towards the total synthesis of tedanolide: an efficient assembly of the C1–C11 subunit

✍ Scribed by Teck-Peng Loh; Li-Chun Feng

• Publisher: Elsevier Science
• Year: 2001
• Tongue: French
• Weight: 93 KB
• Volume: 42
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)01169-8

✦ Synopsis

The C 1 -C 11 subunit of tedanolide was constructed using a boron-mediated syn aldol reaction as the key step to control the C 6 and C 7 stereocenters. Other features of this work include the asymmetric Sharpless dihydroxylation to incorporate the C 2 , C 3 hydroxyl groups, selective protection of the hydroxyl group at C 2 as well as the usage of a tert-butyl ester to tolerate the attack of Grignard and enolate reagents.