Asymmetric total syntheses of naturally occurring α, β-enone-containing RALs, L-783290 and L-783277 through intramolecular base-mediated macrolactonization reaction. Issue 12 (12th March 2020)

• Record Type: Journal Article
• Authors: Chakraborty, Joy; Ghosh, Ankan; Nanda, Samik
• Is Part Of: Organic & biomolecular chemistry. Volume 18:Issue 12(2020)
• Page Start: 2331
• Page End: 2345
• Publication Date: 2020-03-12
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d0ob00237b
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Asymmetric total synthesis of two naturally occurring α, β-enone containing RALs, L-783290 and L-783277 is described in this article. 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.