Open AccessPyrrole Strategy for the γ-Lactam-Containing Stemona Alkaloids: (±)Stemoamide, (±)Tuberostemoamide, and (±)Sessilifoliamide A
Author(s) -
Xianglin Yin,
Kewei Ma,
Ying Dong,
Mingji Dai
Publication year - 2020
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.0c01570
Subject(s) - chemistry , pyrrole , lactam , nucleophile , ring (chemistry) , combinatorial chemistry , stereochemistry , organic chemistry , catalysis
Stemona alkaloids contain family members with diverse structural scaffolds. Many of them feature a γ-lactam ring embedded in their characteristic 5-7-5 fused tricyclic core. Herein a pyrrole strategy was developed to enable the total syntheses of three Stemona alkaloids: (±)stemoamide, (±)tuberostemoamide, and (±)sessilifoliamide A. In these cases, a substituted pyrrole was used as the γ-lactam precursor. A sequential pyrrole oxidation and enamide reduction were realized to convert the pyrrole to the corresponding γ-lactam in those three natural products. The use of a pyrrole in an early stage of the synthesis offers the advantage of rapid construction of the key intermediates by exploiting its nucleophilicity.