Synthetic microbial chemistry, XV. Synthesis of (2E,4R,5S,11R)-(−)-Cladospolide A, a Phytotoxic Macrolide fromCladosporium cladosporioides

✍ Scribed by Mori, Kenji ;Maemoto, Shun'ichi

• Publisher: John Wiley and Sons
• Year: 1987
• Tongue: English
• Weight: 899 KB
• Volume: 1987
• Category: Article
• ISSN: 0947-3440
• DOI: 10.1002/jlac.198719870841

✦ Synopsis

Thc total synthesis of cladwpolidc A [(2E,4R,SS,i lR)-4,S-dihydroxy-l-dodecen-11-olide (la)] was achieved in 16 steps from cthyl (R )-3-hydroxybutanoate (2a).

Cladospolide A is a root-growth inhibitor of lettuce seedlings produced by Cladosporium cladosporioides FI-113 2,3). Its structure and stereochemistry were clarified as depicted in 1 a [(2E,4R,5S,11 R)-4,5-dihydroxy-2-dodecen-11 -olide] by Hirota et al. on the basis of spectroscopic studies and Xray analy~is~-~). It is a 12-membered lactone with a double bond and three chiral centers, and constitutes an interesting target for synthetic studies. A synthesis of 1 a starting from cyclohexylidene-D-glyceraldehyde was reported orally by Ueda and his co-workers6). We also described another synthesis of l a in a preliminary communication7). This paper