Asymmetric Total Synthesis of (−)-Arborisidine and (−)-19-epi-Arborisidine Enabled by a Catalytic Enantioselective Pictet–Spengler Reaction

R Andres, Q Wang, J Zhu - Journal of the American Chemical …, 2020 - ACS Publications
A five-step total synthesis of arborisidine, a caged pentacyclic monoterpene indole alkaloid,
has been accomplished in both racemic and enantioselective manners. The synthesis …

Asymmetric Total Synthesis of (+)-Alstonlarsine A

JJ Yao, R Ding, X Chen, H Zhai - Journal of the American …, 2022 - ACS Publications
The first asymmetric total synthesis of (+)-alstonlarsine A has been realized. The prominent
features of the current synthesis include the following:(i) a Pd/self-adaptable ligand complex …

Asymmetric total syntheses of the akuammiline alkaloids (−)‐strictamine and (−)‐rhazinoline

W Li, Z Chen, D Yu, X Peng, G Wen… - Angewandte …, 2019 - Wiley Online Library
Strictamine and rhazinoline are representative methanoquinolizidine‐containing
akuammiline alkaloids that possess different stereochemistry at the C16 position. A unified …

Total synthesis of (+)-arborisidine

Z Zhou, AX Gao, SA Snyder - Journal of the American Chemical …, 2019 - ACS Publications
The first total synthesis of arborisidine, a unique Kopsia indole alkaloid possessing a fully
substituted cyclohexanone ring system with two quaternary carbons, has been achieved in …

Total syntheses of echitamine, akuammiline, rhazicine, and pseudoakuammigine

X Zhang, BN Kakde, R Guo, S Yadav… - Angewandte Chemie …, 2019 - Wiley Online Library
Abstract Echitamine (1) and akuammiline (2) are representative members of a fascinating
class of monoterpenoid indole alkaloids. We report the syntheses of 2 and its congener …

[HTML][HTML] Monoterpene indole alkaloids from Vinca minor L.(Apocynaceae): Identification of new structural scaffold for treatment of Alzheimer's disease

R Vrabec, J Maříková, M Ločárek, J Korábečný… - Phytochemistry, 2022 - Elsevier
One undescribed indole alkaloid together with twenty-two known compounds have been
isolated from aerial parts of Vinca minor L.(Apocynaceae). The chemical structures of the …

Enantioselective total syntheses of methanoquinolizidine-containing akuammiline alkaloids and related studies

E Picazo, LA Morrill, RB Susick, J Moreno… - Journal of the …, 2018 - ACS Publications
The akuammiline alkaloids are a structurally diverse class of bioactive natural products
isolated from plants found in various parts of the world. A particularly challenging subset of …

Terminating E-ring cyclizations for caged indole alkaloids: The secret to success?

R Kielawa, SA Snyder - Tetrahedron Letters, 2024 - Elsevier
Achieving the synthesis of densely-functionalized, cage-like alkaloids has long proven quite
challenging, with the success of individual events often being acutely sensitive to minute …

Gold (I)-Catalyzed Cascade Cyclization of Alkynyl Indoles for the Stereoselective Construction of the Quaternary Carbon Center of Akuammiline Alkaloids

N Hashimoto, J Taguchi, N Arichi, S Inuki… - The Journal of Organic …, 2023 - ACS Publications
A gold-catalyzed cyclization reaction of alkynyl-indoles has been developed for the
stereoselective construction of the quaternary carbon center of fused indolines. This reaction …

Total Syntheses of Pleiocarpamine, Normavacurine, and C-Mavacurine

K Sato, N Kogure, M Kitajima, H Takayama - Organic letters, 2019 - ACS Publications
The total syntheses of C-mavacurine-type indole alkaloids,(±)-pleiocarpamine,(±)-
normavacurine, and (±)-C-mavacurine, were accomplished. The key step in the syntheses …