Total synthesis of (±)-Vertine with Z-selective RCM as a key step

被引：19

作者：

Chausset-Boissarie, Laetitia ^{[1
]}

Arvai, Roman ^{[1
]}

Cumming, Graham R. ^{[1
]}

Besnard, Celine ^{[1
]}

Kuendig, E. Peter ^{[1
]}

机构：

[1] Univ Geneva, Dept Organ Chem, CH-1211 Geneva, Switzerland

来源：

CHEMICAL COMMUNICATIONS | 2010年 / 46卷 / 34期

基金：

瑞士国家科学基金会;

关键词：

METHOXYMETHYL MOM ETHERS; CROSS-COUPLING REACTIONS; RING-CLOSING METATHESIS; HEIMIA-SALICIFOLIA; LYTHRACEAE ALKALOIDS; ORGANOBORON COMPOUNDS; DEPROTECTION; EFFICIENT; CHEMOTAXONOMY; ALCOHOLS;

D O I：

10.1039/c0cc01885f

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A concise total synthesis of the strained pentacyclic alkaloid (+/-)-Vertine has been achieved in eleven steps with the key steps being pelletierine condensation, Suzuki-Miyaura coupling, and ring-closing metathesis.

引用

页码：6264 / 6266

页数：3

共 50 条

[31] Grubbs' RCM in the total synthesis of the microtubule stabilizing drug laulimalide
Mulzer, J
Öhler, E
Enev, VS
Hanbauer, M
ADVANCED SYNTHESIS & CATALYSIS, 2002, 344 (6-7) : 573 - 584
[32] Z-selective, anti-Markovnikov addition of alkoxides to terminal alkynes: an electron transfer pathway?
Cuthbertson, James
Wilden, Jonathan D.
TETRAHEDRON, 2015, 71 (25) : 4385 - 4392
[33] Mechanism of Z-Selective Olefin Metathesis Catalyzed by a Ruthenium Monothiolate Carbene Complex: A DFT Study
Nelson, John W.
Grundy, Lara M.
Dang, Yanfeng
Wang, Zhi-Xiang
Wang, Xiaotai
ORGANOMETALLICS, 2014, 33 (16) : 4290 - 4294
[34] Recent Developments in Z-Selective Olefin Metathesis Reactions by Molybdenum, Tungsten, Ruthenium, and Vanadium Catalysts
Dawood, Kamal M.
Nomura, Kotohiro
ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (08) : 1970 - 1997
[35] First stereoselective total synthesis of decarestrictine O via RCM protocol
Krishna, Palakodety Radha
Rao, T. Jagannadha
TETRAHEDRON LETTERS, 2010, 51 (31) : 4017 - 4019
[36] Total synthesis of decarestrictine I and botryolide B via RCM protocol
Krishna, Palakodety Radha
Rao, T. Jagannadha
ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (14) : 3130 - 3132
[37] Z-Selective Dienylation Enables Stereodivergent Construction of Dienes and Unravels a Ligand-Driven Mechanistic Dichotomy
Dang, Hang T.
Nguyen, Viet D.
Haug, Graham C.
Vuong, Ngan T. H.
Arman, Hadi D.
Larionov, Oleg, V
ACS CATALYSIS, 2021, 11 (03): : 1042 - 1052
[38] Z-Selective Pd-catalyzed 2,2,2-trifluoroethylation of acrylamides at room temperature
Ruyet, Louise
Lapuh, Maria I.
Koshti, Vijay S.
Foldesi, Tamas
Jubault, Philippe
Poisson, Thomas
Novak, Zoltan
Besset, Tatiana
CHEMICAL COMMUNICATIONS, 2021, 57 (51) : 6241 - 6244
[39] A Concise Total Synthesis of (-)-Maoecrystal Z
Cha, Jacob Y.
Yeoman, John T. S.
Reisman, Sarah E.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (38) : 14964 - 14967
[40] Chiral Atropisomeric-NHC Catechodithiolate Ruthenium Complexes for Z-Selective Asymmetric Ring-Opening Cross Metathesis of Exo-Norbornenes
Morvan, Jennifer
Bouetard, Dylan
Kong, Lingyu
Chou, Yajie
Vives, Thomas
Albalat, Muriel
Roisnel, Thierry
Crevisy, Christophe
Nava, Paola
Humbel, Stephane
Vanthuyne, Nicolas
Clavier, Herve
Mauduit, Marc
CHEMISTRY-A EUROPEAN JOURNAL, 2023, 29 (28)

← 1 2 3 4 5 →