669010-31-5Relevant academic research and scientific papers
First Total Synthesis of Antimitotic Compound, (+)-Phomopsidin
Suzuki, Takahiro,Usui, Kenji,Miyake, Yoshiharu,Namikoshi, Michio,Nakada, Masahisa
, p. 553 - 556 (2004)
(Equation presented) The first total synthesis of (+)-phomopsidin has been achieved via a diastereoselective transannular Diels-Alder (TADA) reaction. Key steps in the synthesis include diastereoselective ynone reduction with (-)-α-pinene and 9-BBN, macrocyclization by E-selective intramolecular Horner-Wadsworth-Emmons (HWE) reaction, as well as carbometalation under Wipf's conditions, followed by HWE reaction at low temperature to selectively construct the (E)-1-methylpropenyl and (1E,2E)-4-carboxy-1,3-butadienyl substituents.
