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A Second Generation Synthesis of Roseophilin and Chromophore Analogues

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Fürstner,  Alois
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Gastner,  Thomas
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Weintritt,  Holger
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Fürstner, A., Gastner, T., & Weintritt, H. (1999). A Second Generation Synthesis of Roseophilin and Chromophore Analogues. The Journal of Organic Chemistry, 64(7), 2361-2366. doi:10.1021/jo982088t.


Cite as: https://hdl.handle.net/11858/00-001M-0000-0024-21FE-1
Abstract
A concise, flexible, and high-yielding synthesis of the macrocyclic compound 4 is outlined which served as a key intermediate in a previous total synthesis of the antitumor active alkaloid roseophilin 1. The key steps of this approach consist of a Pd(0)-catalyzed reaction of vinyloxirane 6 with sulfone 7 and in a subsequent ring closing metathesis (RCM) reaction for the formation of the 13-membered ring catalyzed by the ruthenium carbene Cl2(PCy3)2Ru=CHCH=CPh2 introduced by Grubbs. Moreover, nitrile ylide cycloaddition reactions are used for the preparation of roseophilin side chain mimics. Finally, the synthesis of various chromophore analogues of 1 is reported, including deschloro-desmethoxyroseophilin 12 which is the most elaborate derivative of this complex target reported so far.