Journal
ORGANIC LETTERS
Volume 23, Issue 1, Pages 93-96Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c03766
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Funding
- National Natural Science Foundation of China [21722206, 21702166, 21672171]
- Youth Innovation Team of Shaanxi Universities
- Scientific Fund of Northwest AF University [Z111021501, Z109021600]
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The asymmetric synthesis of ent-fissistigmatin C was achieved in 12 steps, with key stereoselective linking between the flavonoid and sesquiterpenoid fragments. The synthesis also featured an unprecedented final-stage radical cascade, allowing for the simultaneous establishment of the trans-decalin framework through forging two consecutive C-C bonds in one step.
The asymmetric synthesis of ent-fissistigmatin C is successively accomplished in 12 steps (longest linear sequence (LLS)). Relying on the enantioselective coupling of aliphatic aldehyde with 2-hydroxychalcone promoted by cooperative organocatalysts, the pivotal linkage of ent-fissistigmatin C between the flavonoid and the sesquiterpenoid fragment was stereoselectively established. An unprecedented final-stage radical cascade was also featured in this synthesis, which enabled the simultaneous establishment of the trans-decalin framework via forging two consecutive C-C bonds in one step.
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