Journal
ORGANIC PROCESS RESEARCH & DEVELOPMENT
Volume 15, Issue 5, Pages 1149-1162Publisher
AMER CHEMICAL SOC
DOI: 10.1021/op200112g
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- USDA ARS Southern Regional Research Center
- Ohio Soybean Council
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Scaled-up procedures and preparation of glyceollin I in multigrarn quantities are described. The synthesis features construction of a cis-fused ring system in high enantiomeric excess after Sharpless asymmetric dihydroxylation of a key intermediate that is initially produced by an intramolecular Wittig reaction to afford the requisite alkene while simultaneously forming the first ring. The overall yield is 12% after 11 steps.
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