An Approach to the Carbon Backbone of Bielschowskysin, Part 2: Non‐Photochemical Strategy. Issue 36 (19th November 2013)

• Record Type: Journal Article
• Authors: Farcet, Jean‐Baptiste; Himmelbauer, Martin; Mulzer, Johann
• Is Part Of: European journal of organic chemistry. Issue 36(2013)
• Page Start: 8245
• Page End: 8252
• Publication Date: 2013-11-19
• Subjects: Total synthesis -- Natural ­products -- Terpenoids -- Chromium -- Hydroalumination; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201300870
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: The stereocontrolled synthesis of complex and highly substituted polycyclic synthetic precursor2 of the diterpene bielschowskysin is presented. Key steps include a regio‐ and stereoselective hydroalumination as well as an optimized Cr/Ni‐mediated carbon–carbon bond formation between two complex fragments to establish the northern hemisphere of the natural product. Abstract : An approach to the northern section of the complex diterpenoid bielschowskysin is described. Formation of the dihydrofuran ring moiety was achieved through stereoselective epoxidation, followed by alkyne opening and stereoselective formation of a vinyl halide suitable for chromium‐mediated coupling. A final oxidation step furnished the hemiacetal.