Stereoselective synthesis of the C16–C25 fragment of alchivemycins A and B. (22nd June 2021)

• Record Type: Journal Article
• Authors: Liao, Daohong; Yang, Shaoqiang; Ma, Kaiqing; Wang, Xiaoming; Lei, Xiaoguang
• Is Part Of: Tetrahedron letters. Volume 74(2021)
• Publication Date: 2021-06-22
• Subjects: Alchivemycin A -- Polyketide -- Total synthesis -- Dihydroxylation -- Stereoselective; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2021.153156
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Enantioselective route for the synthesis of the C16–C25 fragment of alchivemycins A and B. Effective use of furan as a E -but-2-ene-1, 4-dione surrogate. Highly diastereoselective dihydroxylation as key reaction for vicinal polyol formation. Transition-metal free allylic substitution between Grignard reagent and tosylate. Abstract: An enantioselective route for the efficient synthesis of the key C16–C25 fragment of alchivemycins A and B is described. The route features an Achmatowicz-type rearrangement of furan and a highly enantio - and diastereoselective dihydroxylation as key reactions.