Enantioselective total synthesis of (+)-stephadiamine through bioinspired aza-benzilic acid type rearrangement

M Odagi, T Matoba, K Hosoya… - Journal of the American …, 2021 - ACS Publications
… the first enantioselective total syntheses of the hasubanan alkaloid (−)-metaphanine and the
norhasubanan alkaloid (+)-stephadiamine. … pathway of (+)-stephadiamine, we found that (−)-…

Enantioselective Total Synthesis of (+)-Stephadiamine

B Yang, G Li, Q Wang, J Zhu - Journal of the American Chemical …, 2023 - ACS Publications
… and considered (+)-stephadiamine (1) as an ideal target to initiate our research program.
Shown in Scheme 1 is the retrosynthetic analysis of stephadiamine (1) featuring this strategic …

Total synthesis of the norhasubanan alkaloid stephadiamine

N Hartrampf, N Winter, G Pupo, BM Stoltz… - Journal of the …, 2018 - ACS Publications
… (+)-Stephadiamine is an unusual alkaloid isolated from the vine … Here, we present the first
total synthesis of stephadiamine, which … Useful building blocks for the asymmetric synthesis of …

Asymmetric Total Synthesis of Hasubanan Alkaloids: Periglaucines A–C, N,O‐Dimethyloxostephine and Oxostephabenine

S Ding, Y Shi, B Yang, M Hou, H He… - Angewandte Chemie …, 2023 - Wiley Online Library
… Recently, an enantioselective dearomatizative Michael … synthetic strategy to facilitate the
total synthesis of all three sub-… The total synthesis of stephadiamine (9), the only example of a …

Total Synthesis Provides Strong Evidence: Xestocyclamine A is the Enantiomer of Ingenamine

Z Meng, A Fürstner - Journal of the American Chemical Society, 2020 - ACS Publications
… Xestocyclamine A ((−)-1) is featured prominently in a biosynthesis pathway leading to a
large family of polycyclic alkaloids. The first total synthesis now proves that the structure of this …

[HTML][HTML] Unified divergent strategy towards the total synthesis of the three sub-classes of hasubanan alkaloids

G Li, Q Wang, J Zhu - Nature Communications, 2021 - nature.com
… Elegant asymmetric synthesis of hasubanan alkaloids have … enantioselective total syntheses
of four representative members. The synthesis is characterized by catalytic enantioselective

Total Synthesis of Yuzurine-type Alkaloid Daphgraciline

LX Li, L Min, TB Yao, SX Ji, C Qiao… - Journal of the …, 2022 - ACS Publications
… hand, we then explored the asymmetric formation of (+)… overall yield. It is envisaged that the
use of the chiral azabicyclo[4.3.1] ring system (+)-7 will enable the asymmetric total synthesis

Enantioselective Total Synthesis of Cepharatines via Bioinspired Ring Reconstruction

M Odagi, T Matoba, K Nagasawa - The Journal of Organic …, 2021 - ACS Publications
We describe enantioselective total syntheses of cepharatines AD, members of the hasubanan
alkaloid family, which feature an unusual tetracyclic skeleton including an azabicyclo[3.3.1]…

A unified approach to polycyclic alkaloids of the ingenamine estate: total syntheses of keramaphidin B, ingenamine, and nominal njaoamine I

Z Meng, SM Spohr, S Tobegen, C Farès… - Journal of the …, 2021 - ACS Publications
… This decision paid valuable dividends, as it ultimately allowed compound 9 to be used as
a common intermediate for the total synthesis of nominal xestocyclamine A ((−)-3) and ent-…

[HTML][HTML] Enantioselective formation of quaternary carbon stereocenters in natural product synthesis: a recent update

C Li, SS Ragab, G Liu, W Tang - Natural Product Reports, 2020 - pubs.rsc.org
… employed for the asymmetric total synthesis of three … The synthesis started with preparation
of spirooxindole 2 in a … finished the first asymmetric total synthesis of stephadiamine. …