Construction of Iterative Tetrahydrofuran Ring Units and Total Synthesis of (+)-Goniocin.
Cytotoxic acetogenin (+)-goniocin has been synthesized in 17 steps from (R)-O-tritylglycidol. The core structure of the contiguous C22-C10 threo-trans-threo-trans-threo-trans-tris-tetrahydrofuran (THF) ring involving an iterative THF-ring unit was synthesized. An iterative THF ring unit was constructed from an alkenyl-substituted THF ring in four steps including a Pd(II)-catalyzed ring-closing reaction and cross-metathesis. This method is general and allows the preparation of both trans-threo-trans- and trans-threo-cis-THF ring units flexibly.
Kyoto Pharmaceutical University , Yamashina, Kyoto 607-8412, Japan.
Ai
A
Suzuki
Kyoto Pharmaceutical University , Yamashina, Kyoto 607-8412, Japan.
Mai
M
Sasaki
Kyoto Pharmaceutical University , Yamashina, Kyoto 607-8412, Japan.
Tetsuya
T
Nakagishi
Kyoto Pharmaceutical University , Yamashina, Kyoto 607-8412, Japan.
Tsuyoshi
T
Ueda
Kyoto Pharmaceutical University , Yamashina, Kyoto 607-8412, Japan.
Naoyuki
N
Hoshiya
Kyoto Pharmaceutical University , Yamashina, Kyoto 607-8412, Japan.
Jun'ichi
J
Uenishi