(+)-Rimocidin Synthetic Studies: Construction of the C(1−27) Aglycone Skeleton
Authors:
- Amos B. SmithASAmos B. Smith
- Megan A. FoleyMFMegan A. Foley
- Shuzhi DongSDShuzhi Dong
- Alia OrbinAOAlia Orbin
Open Access
- 21 July 2009
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 74 (16) , 5987-6001
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 SN2/SN2′ 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.Keywords
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