Journal
RSC ADVANCES
Volume 4, Issue 29, Pages 14979-14984Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c3ra47465h
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Funding
- National Key Project for Basic Research [2010CB126106]
- National Natural Science Foundation of China [21132003, 21121002, 21372131, 21002053]
- Tianjin Natural Science Foundation [11JCZDJC20500]
- Specialized Research Fund for the Doctoral Program of Higher Education [20130031110017]
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A concise and efficient enantioselective strategy to synthesize two typical phenanthroindolizidine alkaloids, 14-hydroxyantofine and antofine, was developed, featuring an asymmetric deprotonation/diastereoselective carbonyl addition sequence during which the formation of a chiral C-13a center and connection of pyrrolidine and phenanthrene moieties were achieved efficiently in one step. The absolute configuration of the C-13a stereocenter can be delicately controlled by using different enantiomers of sparteine, both of which are commercially available.
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