Total synthesis and anti-inflammatory activity of stemoamide-type alkaloids including totally substituted butenolides and pyrroles

Y Soda, Y Sugiyama, S Sato, K Shibuya, J Saegusa… - …, 2023 - thieme-connect.com
Totally substituted butenolide including two tetrasubstituted olefins is a distinct structural
motif seen in Stemona alkaloids, but efficient methods for its synthesis are not well …

Pyrrole Strategy for the γ-Lactam-Containing Stemona Alkaloids: (±)Stemoamide, (±)Tuberostemoamide, and (±)Sessilifoliamide A

X Yin, K Ma, Y Dong, M Dai - Organic letters, 2020 - ACS Publications
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 …

Unified total synthesis of pentacyclic stemoamide-type alkaloids

Y Soda, Y Sugiyama, M Yoritate, H Tajima… - Organic …, 2020 - ACS Publications
The collective synthesis of pentacyclic stemoamide-type alkaloids is recognized as a
daunting task despite high demand for a comprehensive biological profiling of these natural …

[HTML][HTML] Total syntheses of seven stemoamide-type Stemona alkaloids

T Shi, F Cao, J Chen, X Wang, G Yin… - Organic Chemistry …, 2022 - pubs.rsc.org
Six Stemona alkaloids were synthesized racemically using stemoamide, obtained via a
cascade cyclization or our reported transannular cyclization of parvistemoamide, as the …

Undescribed matrine-type alkaloids from Sophora alopecuroides with anti-inflammatory activity

D Luo, JW Zou, JH Wang, H Tian, HY Xie, TX Zhu… - Phytochemistry, 2024 - Elsevier
A phytochemical investigation on the alkaloid fractions of Sophora alopecuroides L. led to
the production of 11 undescribed matrine-type alkaloids, sophaloseedlines I–S (1− 11), 12 …

Asymmetric total syntheses and biological studies of tuberostemoamide and sessilifoliamide A

Y Hou, T Shi, Y Yang, X Fan, J Chen, F Cao… - Organic letters, 2019 - ACS Publications
The first asymmetric total syntheses of tuberostemoamide, sessilifoliamide A, and their
epimers have been accomplished via the common intermediate ethylstemoamide. The …

Free-radical approaches to stemoamide and analogues

N Bogliotti, PI Dalko, J Cossy - The Journal of Organic Chemistry, 2006 - ACS Publications
Two approaches allowing access to the tricyclic stemona backbone are presented. Both
approaches rely on a free-radical cyclization reaction as the key step. In the formal synthesis …

A Rapid Synthetic Approach to the ABCD Core of the Stemona Alkaloids

RL Connelly, JP Knowles, KI Booker-Milburn - Organic letters, 2018 - ACS Publications
A new Lewis acid-assisted Brønsted acid cascade approach for the stereoselective
formation of the tetracyclic Stemona alkaloid skeleton is described in five steps from epoxide …

Strategies for the Synthesis of Stemona Alkaloids

R Alibés, M Figueredo - European Journal of Organic Chemistry, 2009 - Wiley Online Library
The extracts of several plants of the Stemonaceae family have long been used in Asian
countries against differentdiseases and for their antiparasitic properties. Significant …

Unified total synthesis of stemoamide-type alkaloids by chemoselective assembly of five-membered building blocks

M Yoritate, Y Takahashi, H Tajima… - Journal of the …, 2017 - ACS Publications
A unified total synthesis of stemoamide-type alkaloids is reported. Our synthetic approach
features the chemoselective convergent assembly of five-membered building blocks via …