Journal
MARINE DRUGS
Volume 19, Issue 5, Pages -Publisher
MDPI
DOI: 10.3390/md19050247
Keywords
total synthesis; structural reassignment; laingolide A
Categories
Funding
- National Natural Science Foundation of China [21772009, 21901013]
- Shenzhen Peacock Plan [KQTD2015071714043444]
- Shenzhen Science and Technology Innovation Commission [JCYJ20170818090017617]
- GDNSF [2014B030301003]
- China Postdoctoral Science Foundation [2019M660286]
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The asymmetric total synthesis of four diastereomers of laingolide A enabled the unambiguous assignment of the natural product's stereochemistry. The key features of the convergent, fully stereocontrolled approach included a copper-catalysed stereospecific Kumada-type coupling, a Julia-Kocienski olefination, and an RCM/alkene migration sequence to obtain the desired macrocyclic enamide.
The asymmetric total synthesis of four diastereomers of laingolide A was achieved, which led to the unambiguous assignment of the stereochemistry of the natural product. The salient features of the convergent, fully stereocontrolled approach were a copper-catalysed stereospecific Kumada-type coupling, a Julia-Kocienski olefination and an RCM/alkene migration sequence to access the desired macrocyclic enamide.
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