Total Synthesis of a New Cytotoxic Acetogenin, Jimenezin, and the Revised Structure
- 17 November 1999
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 1 (12) , 2025-2028
- https://doi.org/10.1021/ol991200m
Abstract
The first total synthesis of jimenezin was achieved by using carbohydrates as chiral building blocks, thus revising the proposed structure 1 to 2. The key steps in this synthesis include an efficient construction of the THP−THF fragments 3 and 16 through a stereoselective condensation between the pyranyl aldehyde 5 and the acetylene derivative 6, and a palladium-catalyzed coupling reaction of 3 or 16 with a terminal butenolide 4.Keywords
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