4.8 Review

The development of endo-selective epoxide-opening cascades in water

Journal

CHEMICAL SOCIETY REVIEWS
Volume 38, Issue 11, Pages 3175-3192

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/b816697h

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Funding

  1. NIGMS NIH HHS [R01 GM072566, R01 GM072566-05] Funding Source: Medline
  2. NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES [R01GM072566] Funding Source: NIH RePORTER

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This tutorial review traces the development of endo-regioselective epoxide-opening reactions in water. Templated, water-promoted epoxide-opening cyclization reactions can offer rapid access to subunits of the ladder polyethers, a fascinating and complex family of natural products. This review may be of interest to those curious about the ladder polyethers and their hypothesized biogenesis, about organic reactions in water, and about the development and application of cascade reactions in organic synthesis.

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