Formal total synthesis of (+)-salicylihalamides A and B: a combined chiral pool and RCM strategy |
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Authors: | Yang KyoungLang Blackman Burchelle Diederich Wibke Flaherty Patrick T Mossman Craig J Roy Subho Ahn Yu Mi Georg Gunda I |
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Affiliation: | Department of Medicinal Chemistry, Center for Cancer Experimental Therapeutics, and the Drug Discovery Program, Higuchi Biosciences Center, University of Kansas, 1251 Wescoe Hall Drive, Lawrence, Kansas 66045-7582, USA. |
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Abstract: | The formal total synthesis of the (+)-salicylihalamides A and B is detailed, utilizing a chiral pool approach to generate the three stereogenic centers and a ring-closing metathesis (RCM) for the formation of the macrocyclic ring structure. Starting from a known glucose-derived alcohol, the formal total synthesis was achieved in an efficient 13-step protocol in 26% overall yield. It was found that substitution at the remote phenolic group significantly influenced the ratio of the E- and Z-double bond products in the RCM step. The introduction of phenol protecting groups provided E-isomers preferentially and also enhanced the rates of the RCM reactions. |
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