期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 78, 期 21, 页码 10885-10893出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo4018777
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资金
- National Natural Science Foundation of China [21290180, 20972007]
- National Basic Research Program of China (973 Program) [2010CB833200]
- State Key Laboratory of Drug Research
We report the enantioselective total synthesis of (+)-lysergic acid using two different strategies, which featured three metal-catalyzed reactions for the construction of the BCD three rings, involving Pd-catalyzed indole synthesis for the construction of the B ring, a ring-closing metathesis reaction for the formation of the D ring, and an intramolecular Heck reaction to forge the C ring. In synthetic strategy I, the synthesis was achieved in 20 steps following the ring construction sequence of BDC. In synthetic strategy II, the synthetic route was shortened to only 12 steps by following the ring construction sequence of DBC and using a 4-chlorotryptophan derivative for the intramolecular Heck reaction. Moreover, we also discussed an unsuccessful synthetic strategy.
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