Efficient Synthesis of (-)-Hanishin, (-)-Longamide B, and (-)-Longamide B Methyl Ester through Piperazinone Formation from 1,2-Cyclic Sulfamidates

We describe a simple chiral-pool synthesis of (-)-longamide B, (-)-longamide B methyl ester, and (-)-hanishin. The key feature of the total synthesis is the formation of a piperazinone from a 1,2-cyclic sulfamidate and methyl 2-pyrrolecarboxylate, which permits efficient construction of the pyrrolop...

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Bibliographic Details
Published inSynlett Vol. 27; no. 4; pp. 616 - 620
Main Authors Shiokawa, Zenyu, Inuki, Shinsuke, Fukase, Koichi, Fujimoto, Yukari
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.03.2016
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
POTENT
longamide B
asymmetric synthesis
heterocycles
piperazinones
NATURAL-PRODUCTS
hanishin
LACTAMS
sulfamidates
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Summary:We describe a simple chiral-pool synthesis of (-)-longamide B, (-)-longamide B methyl ester, and (-)-hanishin. The key feature of the total synthesis is the formation of a piperazinone from a 1,2-cyclic sulfamidate and methyl 2-pyrrolecarboxylate, which permits efficient construction of the pyrrolopiperazinone core scaffold.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0035-1560988