Asymmetric total syntheses of naturally occurring α,β-enone-containing RALs, L-783290 and L-783277 through
Joy Chakraborty1, Ankan Ghosh2, Samik Nanda1
1Department of Chemistry, Indian Institute of Technology Kharagpur, Kharagpur, India. snanda@chem.iitkgp.ac.in.
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 C7'-C8' olefinic unsaturation in L-783290. An enantiopure alkyne addition to the aldehyde followed by Z-selective partial reduction was employed to construct the C7'-C8' olefinic unsaturation in L-783277. Biomimetic lactonization reaction was used to construct the macrolactone core in both the target molecules.
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