A Concise Stereoselective Synthesis of Naturally Occurring d‐Xylo‐C18‐Guggultetrol and its C2‐Epimer. Issue 4 (7th March 2019)

• Record Type: Journal Article
• Authors: Chandra, Naveen; Fernandes, Rodney A.
• Is Part Of: Asian journal of organic chemistry. Volume 8:Issue 4(2019)
• Page Start: 532
• Page End: 536
• Publication Date: 2019-03-07
• Subjects: guggultetrol -- rheumatoid arthritis -- stereoselective synthesis -- dihydroxylation -- natural products; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.201900063
• Languages: English
• ISSNs: 2193-5807

Abstract

Abstract: d ‐Gluconic acid δ‐lactone has served as an economical and commercially available key chiral template for a concise 7‐step stereoselective synthesis of d ‐ xylo ‐ and d ‐ lyxo ‐configured guggultetrols. The key steps involved are a one‐pot conversion of d ‐gluconic acid δ‐lactone to γ‐vinyl‐β‐hydroxy‐γ‐lactone, a chain extension through a Grignard reaction and a diastereoselective Sharpless asymmetric dihydroxylation. Abstract : Playing the xylo phone : A concise stereoselective synthesis of D‐ xylo‐ and D‐ lyxo‐ guggultetrols has been achieved from commercially available d ‐gluconic acid δ‐lactone, involving a one‐pot conversion to γ‐vinyl‐β‐hydroxy‐γ‐lactone, chain extension, and a diastereoselective dihydroxylation.