Enantioselective Total Synthesis of (+)-Iso-A82775C, a Proposed Biosynthetic Precursor of Chloropupukeananin

2017 ◽  
Vol 19 (4) ◽  
pp. 922-925 ◽  
Author(s):  
Takahiro Suzuki ◽  
Soichiro Watanabe ◽  
Susumu Kobayashi ◽  
Keiji Tanino
Keyword(s):  
Total Synthesis ◽  
Enantioselective Total Synthesis ◽  
Biosynthetic Precursor

scholarly journals Bioinspired Oxidative Cyclization of the Geissoschizine Skeleton for the Enantioselective Total Synthesis of Mavacuran Alkaloids

2019 ◽  
Author(s):  
Maxime Jarret ◽  
Victor Turpin ◽  
Aurélien Tap ◽  
Jean-Francois Gallard ◽  
Cyrille Kouklovsky ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Oxidative Coupling ◽  
Indole Alkaloids ◽  
Oxidative Cyclization ◽  
Total Syntheses ◽  
Enantioselective Total Synthesis ◽  
Biosynthetic Precursor ◽  
Monoterpene Indole Alkaloids ◽  
Coupling Approach

We report the enantioselective total syntheses of mavacurans alkaloids, (+)-taberdivarine H, (+)-16-hydoxymethyl-pleiocarpamine, (+)-16-epi-pleiocarpamine, and their postulated biosynthetic precursor 16-formyl-pleiocarpamine. This family of monoterpene indole alkaloids is a target of choice since some of its members are subunits of intricate bisindole alkaloids such as bipleiophylline. Inspired by the biosynthetic hypothesis, we explored an oxidative coupling approach from the geissoschizine framework to form the N1-C16 bond. Quaternization of the aliphatic nitrogen was key to achieve the oxidative coupling induced by KHMDS/I<sub>2 </sub>since<sub> </sub>it hides the nucleophilicity of the aliphatic nitrogen and locks the required cis conformation.

scholarly journals Bioinspired Oxidative Cyclization of the Geissoschizine Skeleton for the Enantioselective Total Synthesis of Mavacuran Alkaloids

2019 ◽  
Author(s):  
Maxime Jarret ◽  
Victor Turpin ◽  
Aurélien Tap ◽  
Jean-Francois Gallard ◽  
Cyrille Kouklovsky ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Oxidative Coupling ◽  
Indole Alkaloids ◽  
Oxidative Cyclization ◽  
Total Syntheses ◽  
Enantioselective Total Synthesis ◽  
Biosynthetic Precursor ◽  
Monoterpene Indole Alkaloids ◽  
Coupling Approach

We report the enantioselective total syntheses of mavacurans alkaloids, (+)-taberdivarine H, (+)-16-hydoxymethyl-pleiocarpamine, (+)-16-epi-pleiocarpamine, and their postulated biosynthetic precursor 16-formyl-pleiocarpamine. This family of monoterpene indole alkaloids is a target of choice since some of its members are subunits of intricate bisindole alkaloids such as bipleiophylline. Inspired by the biosynthetic hypothesis, we explored an oxidative coupling approach from the geissoschizine framework to form the N1-C16 bond. Quaternization of the aliphatic nitrogen was key to achieve the oxidative coupling induced by KHMDS/I<sub>2 </sub>since<sub> </sub>it hides the nucleophilicity of the aliphatic nitrogen and locks the required cis conformation.

scholarly journals Enantioselective Total Synthesis of (+)‐Garsubellin A

2021 ◽  
Author(s):  
Dongseok Jang ◽  
Minchul Choi ◽  
Jinglong Chen ◽  
Chulbom Lee
Keyword(s):  
Total Synthesis ◽  
Enantioselective Total Synthesis

Enantioselective Total Synthesis of ( – )‐Spiroxins A, C and D

2021 ◽  
Author(s):  
Xin Shu ◽  
Chong-Chong Chen ◽  
Tao Yu ◽  
Jiayi Yang ◽  
Xiangdong Hu
Keyword(s):  
Total Synthesis ◽  
Enantioselective Total Synthesis

Unified enantioselective total synthesis of 3,6-dioxygenated diketopiperazine natural products, diatretol and lepistamides A, B and C

2021 ◽  
Vol 67 ◽  
pp. 152895
Author(s):  
Shu Takahashi ◽  
Aoi Kimishima ◽  
Tomoyasu Hirose ◽  
Takeshi Yamada ◽  
Akihiro Sugawara ◽  
...  
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Enantioselective Total Synthesis

Enantioselective total synthesis of sesquiterpenoid phellilane L and its diastereomer

Tetrahedron ◽  
2021 ◽  
Vol 87 ◽  
pp. 132110
Author(s):  
Gullapalli Kumaraswamy ◽  
Vankudoth Ramesh ◽  
Swargam Vijaykumar
Keyword(s):  
Total Synthesis ◽  
Enantioselective Total Synthesis

A concise enantioselective total synthesis of rhizoxin D

2002 ◽  
Vol 43 (3) ◽  
pp. 493-497 ◽  
Author(s):  
Ian S. Mitchell ◽  
Gerald Pattenden ◽  
Jeffrey P. Stonehouse
Keyword(s):  
Total Synthesis ◽  
Enantioselective Total Synthesis ◽  
Rhizoxin D

ChemInform Abstract: An Enantioselective Total Synthesis of (+)-Cassiol.

ChemInform ◽  
2010 ◽  
Vol 28 (15) ◽  
pp. no-no
Author(s):  
O. IRIE ◽  
Y. FUJIWARA ◽  
H. NEMOTO ◽  
K. SHISHIDO
Keyword(s):  
Total Synthesis ◽  
Enantioselective Total Synthesis
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