Stereoselective Total Syntheses of Paecilomycins E and F through a Protecting Group Directed Diastereoselective Intermolecular Nozaki–Hiyama–Kishi (NHK) Reaction. Issue 23 (11th July 2014)

• Record Type: Journal Article
• Authors: Mohapatra, Debendra K.; Reddy, D. Sai; Mallampudi, N. Arjunreddy; Yadav, Jhillu S.
• Is Part Of: European journal of organic chemistry. Issue 23(2014)
• Page Start: 5023
• Page End: 5032
• Publication Date: 2014-07-11
• Subjects: Total synthesis -- Natural products -- C–C coupling -- Dihydroxylation -- Olefination -- Cyclization; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201402133
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: An efficient and concise approach to the total syntheses of paecilomycins E (1 ) and F (2 ) is described. A protecting group directed intermolecular diastereoselective Nozaki–Hiyama–Kishi (NHK) reaction, a Julia–Kocienski olefination, a Sharpless asymmetric dihydroxylation, and De Brabander's lactonization protocol are used as the key steps. Abstract : The convergent and concise total syntheses of paecilomycins E and F were achieved through 10 linear steps in high overall yields from known intermediates. A protecting group directed diastereoselective intermolecular Nozaki–Hiyama–Kishi (NHK) reaction, a Julia–Kocienski olefination, a Sharpless asymmetric dihydroxylation, and De Brabander's lactonization protocol were employed as the key steps.