An Approach to the Carbon Backbone of Bielschowskysin, Part 1: Photocyclization Strategy. Issue 36 (19th November 2013)

• Record Type: Journal Article
• Authors: Himmelbauer, Martin; Farcet, Jean‐Baptiste; Gagnepain, Julien; Mulzer, Johann
• Is Part Of: European journal of organic chemistry. Issue 36(2013)
• Page Start: 8214
• Page End: 8244
• Publication Date: 2013-11-19
• Subjects: Natural products -- Total synthesis -- Asymmetric synthesis -- Cycloaddition -- Terpenoids; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201300869
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: Several macrocyclization reaction attempts of highly advanced precursors toward a total synthesis of marine diterpene bielschowskysin are disclosed. Biomimetic [2+2]‐photocyclization reactions were applied to construct the cyclobutane core in these intermediates, which could be accessed along scalable high‐yielding reaction sequences from cheap enantiopure starting‐materials. Abstract : Asymmetric syntheses of various highly functionalized intermediates toward the total synthesis of bielschowskysin (1 ) are described. In particular a biomimetic [2+2]‐photocycloaddition reaction strategy, forming the cyclobutane core, was followed by various macrocyclization reactions attempts.