Preparation of Macrocyclic
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Author(s)
Zhang, Hanmo
Yu, Elsie C.
Torker, Sebastian
Hoveyda, Amir H.
Schrock, Richard Royce
Date Issued
November 2014
Journal
Journal of the American Chemical Society
Publisher
American Chemical Society (ACS)
Citation
Zhang, Hanmo; Yu, Elsie C.; Torker, Sebastian; Schrock, Richard R. and Hoveyda, Amir H. "Preparation of Macrocyclic." Journal of the American Chemical Society 136, no. 47 (November 2014): 16493–16496 © 2014 American Chemical Society
Version
Author's final manuscript
Abstract
The first examples of catalyst-controlled stereoselective macrocyclic ring-closing metathesis reactions that generate Z-enoates as well as (E,Z)- or (Z,E)-dienoates are disclosed. Reactions promoted by 3.0–10 mol % of a Mo-based monoaryloxide pyrrolide complex proceed to completion within 2–6 h at room temperature. The desired macrocycles are formed in 79:21 to >98:2 Z/E selectivity; stereoisomerically pure products can be obtained in 43–75% yield after chromatography. Utility is demonstrated by application to a concise formal synthesis of the natural product (+)-aspicilin.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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DOI of Published Version
https://doi.org/10.1021/ja510768c
