Building multifunctional chiral building blocks from simple starting materials such as D-glutamic acid opens up synthetic routes to natural products.
Chemists in China have made a chiral lactam reagent from inexpensive D-glutamic acid and demonstrated its synthetic prowess in the asymmetric production of a ceramide sphingolipid. This complex natural product is the sex pheromone of hair crab, the team explains, and is one of a group of compounds to exhibit bioactivity in the control of cell growth, maturity, survival and apoptosis. It also inhibits some target enzymes and activates others. The compound has promise as a lead to novel drugs for treating cancer and cell proliferation with analogs having cytotoxicity against tumors.
- Asymmetric synthesis of ceramide sphingolipid based on (2S,3S,4S)- 3,4-dihydroxy-5-(hydroxymethyl)pyrrolidin lactam
W.-F. Huanga, Q.-R. Lia, L.-M. Chaoa, X.-S. Leib, B.-G. Wei,
Tetrahedron Lett. 2010, 51.