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  • Title: (+)-Rimocidin synthetic studies: construction of the C(1-27) aglycone skeleton.
    Author: Smith AB, Foley MA, Dong S, Orbin A.
    Journal: J Org Chem; 2009 Aug 21; 74(16):5987-6001. PubMed ID: 19621880.
    Abstract:
    Assembly of the C(1-27) macrocyclic skeleton of rimocidinolide, the aglycone of (+)-rimocidin (1), has been achieved in convergent fashion. Key features of the synthetic strategy entail application of multicomponent Type I Anion Relay Chemistry (ARC), in conjunction with the S(N)2/S(N)2' reaction manifolds of vinyl epoxides, both employing 2-substituted 1,3-dithianes to construct the C(1-19) carbon backbone. Yamaguchi union of a C(20-27) vinyl borate ester, possessing the all-trans triene, with an advanced C(1-19) vinyl iodide followed by macrocyclization via Suzuki-Miyaura cross-coupling completed construction of the C(1-27) rimocidinolide skeleton.
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