Formal Total Synthesis of (+)-Salicylihalamides A and B: A Combined Chiral Pool and RCM Strategy

Kyoung Lang Yang, Burchelle Blackman, Wibke Diederich, Patrick T. Flaherty, Craig J. Mossman, Subho Roy, Yu Mi Ahn, Gunda I. Georg

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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.

Original languageEnglish (US)
Pages (from-to)10030-10039
Number of pages10
JournalJournal of Organic Chemistry
Volume68
Issue number26
DOIs
StatePublished - Dec 26 2003

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    Yang, K. L., Blackman, B., Diederich, W., Flaherty, P. T., Mossman, C. J., Roy, S., Ahn, Y. M., & Georg, G. I. (2003). Formal Total Synthesis of (+)-Salicylihalamides A and B: A Combined Chiral Pool and RCM Strategy. Journal of Organic Chemistry, 68(26), 10030-10039. https://doi.org/10.1021/jo0301550