Journal
TETRAHEDRON LETTERS
Volume 58, Issue 42, Pages 4011-4013Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2017.09.017
Keywords
Sacrolide; Antimicrobial; Macrolide; Oxylipin; Total synthesis
Categories
Funding
- JSPS KAKENHI [15J02009]
- Platform Project for Supporting Drug Discovery and Life Science Research
- Japan Agency for Medical Research and Development (AMED)
- Grants-in-Aid for Scientific Research [15J02009] Funding Source: KAKEN
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An enantioselective total synthesis of sacrolide A, an antimicrobial and cytotoxic fourteen-membered macrolactonic oxylipin isolated from an edible freshwater cyanobacterium, has been accomplished from a known carboxylic acid in 20% overall yield by a concise ten-step sequence. The key transformations include chiral oxazolidinone-based diastereoselective installation of two hydroxy-bearing stereocenters, the Horner Wadsworth Emmons olefination to construct the full carbon skeleton, and the Shiina macrolactonization to establish the fourteen-membered macrolide structure. (C) 2017 Elsevier Ltd. All rights reserved.
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