Structural determination of montanacin D by total synthesis.
The first total syntheses of acetogenin 3 and its 4 S,8 R-isomer are described. The key step involves intermolecular metathesis of an alpha,beta-unsaturated ketone carrying a tetrahydropyranyl lactone with a tetrahydrofuran derivative. Compound 3 has spectroscopic and physical data consistent with those of natural montanacin D, suggesting that the absolute configuration of the natural product is as shown in 3.
Takahashi
Shunya
S
RIKEN (The Institute of Physical and Chemical Research), Wako, Saitama 351-0198, Japan. shunyat@riken.go.jp
Hongo
Yayoi
Y
Tsukagoshi
Yuki
Y
Koshino
Hiroyuki
H