Asymmetric total syntheses of naturally occurring α,β-enone-containing RALs, L-783290 and L-783277 through intramolecular base-mediated macrolactonization reaction†,10.1039/D0OB00237B

热搜：

Lactoyl-CoA 全氟丁基戊烷白叶藤碱全氟己基辛烷新白叶藤碱壳寡糖特色专题-生物多肽

Asymmetric total syntheses of naturally occurring α,β-enone-containing RALs, L-783290 and L-783277 through intramolecular base-mediated macrolactonization reaction†

Joy Chakraborty,Samik Nanda

Organic & Biomolecular Chemistry Pub Date : 03/09/2020 00:00:00 , DOI:10.1039/D0OB00237B

Abstract

Asymmetric total synthesis of two naturally occurring α,β-enone containing RALs, L-783290 and L-783277 is described in this article. An E-selective Horner–Wadsworth–Emmons (HWE) olefination was used as a key reaction to construct the C_7′–C_8′ olefinic unsaturation in L-783290. An enantiopure alkyne addition to the aldehyde followed by Z-selective partial reduction was employed to construct the C_7′–C_8′ olefinic unsaturation in L-783277. Biomimetic lactonization reaction was used to construct the macrolactone core in both the target molecules.