scholarly journals Towards stereochemical control: A short formal enantioselective total synthesis of pumiliotoxins 251D and 237A

2013 ◽  
Vol 9 ◽  
pp. 2358-2366 ◽  
Author(s):  
Jie Zhang ◽  
Hong-Kui Zhang ◽  
Pei-Qiang Huang
Keyword(s):  
Total Synthesis ◽  
Enantioselective Synthesis ◽  
Ring Closure ◽  
Enantioselective Total Synthesis ◽  
Stereochemical Control ◽  
Stereoselective Addition ◽  
Methylmagnesium Iodide

A concise enantioselective synthesis of the advanced intermediate 5 for the synthesis of pumiliotoxins (Gallagher’s intermediate) is described. The synthesis started from the regio- and trans-diastereoselective (dr = 98:2) reductive 3-butenylation of (R)-3-(tert-butyldimethylsilyloxy)glutarimide 14. After O-desilylation and Dess–Martin oxidation, the resulting keto-lactam 10 was subjected to a highly trans-stereoselective addition of the methylmagnesium iodide to give carbinol 11 as sole diastereomer. An efficient ring closure procedure consisting of ozonolysis and reductive dehydroxylation provided the indolizidine derivative 5, which completed the formal enantioselective total synthesis of pumiliotoxins 251D and 237A.

Enantioselective total synthesis of (−)-kainic acid and (+)-acromelic acid C via Rh(i)-catalyzed asymmetric enyne cycloisomerization

2018 ◽  
Vol 54 (7) ◽  
pp. 727-730 ◽  
Author(s):  
Honghui Lei ◽  
Shan Xin ◽  
Yifan Qiu ◽  
Xumu Zhang
Keyword(s):  
Total Synthesis ◽  
Kainic Acid ◽  
Enantioselective Synthesis ◽  
Enantioselective Total Synthesis ◽  
Synthetic Strategy

A diversity-oriented synthetic strategy for the enantioselective synthesis of (−)-kainic acid and (+)-acromelic acid C is presented.

Enantioselective total synthesis of (+)-arborescidine C and related tetracyclic indole alkaloids using organocatalysis

2017 ◽  
Vol 15 (16) ◽  
pp. 3408-3412 ◽  
Author(s):  
Vishal M. Sheth ◽  
Bor-Cherng Hong ◽  
Gene-Hsiang Lee
Keyword(s):  
Total Synthesis ◽  
Indole Alkaloids ◽  
Enantioselective Synthesis ◽  
Cyclization Reaction ◽  
Enantioselective Total Synthesis

Enantioselective synthesis of (+)-arborescidine C was achieved by the key step of Pictet–Spengler cyclization reaction with a Jacobsen-type thiourea organocatalyst.

scholarly journals Enantioselective total synthesis of (R)-(−)-complanine

2012 ◽  
Vol 8 ◽  
pp. 1695-1699 ◽  
Author(s):  
Krystal A D Kamanos ◽  
Jonathan M Withey
Keyword(s):  
Total Synthesis ◽  
Natural Product ◽  
Causative Agent ◽  
Enantioselective Synthesis ◽  
Marine Natural Product ◽  
Enantioselective Total Synthesis ◽  
Efficient Access

A route is described for the enantioselective synthesis of (R)-(−)-complanine, a marine natural product isolated from Eurythoe complanata, and known to be a causative agent in inflammation. An organocatalytic, asymmetric oxyamination of a homoconjugated all-Z-dienal intermediate provides versatile and efficient access to the natural product.

scholarly journals Enantioselective total synthesis of (−)-colchicine, (+)-demecolcinone and metacolchicine: determination of the absolute configurations of the latter two alkaloids

2017 ◽  
Vol 8 (7) ◽  
pp. 4961-4966 ◽  
Author(s):  
Bo Chen ◽  
Xin Liu ◽  
Ya-Jian Hu ◽  
Dong-Mei Zhang ◽  
Lijuan Deng ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Enantioselective Synthesis ◽  
Enantioselective Total Synthesis ◽  
The Absolute

A highly concise, enantioselective synthesis of (−)-colchicine, the first syntheses of (+)-demecolcinone and metacolchicine, was reported.

Enantioselective total synthesis and biological evaluation of (−)-solanacol

2018 ◽  
Vol 16 (30) ◽  
pp. 5500-5507 ◽  
Author(s):  
L. J. Bromhead ◽  
A. R. Norman ◽  
K. C. Snowden ◽  
B. J. Janssen ◽  
C. S. P. McErlean
Keyword(s):  
Total Synthesis ◽  
Phenyl Ring ◽  
Biological Evaluation ◽  
Enantioselective Synthesis ◽  
Enantioselective Total Synthesis ◽  
Synthesis And Biological Evaluation

An enantioselective synthesis of the phenyl ring-containing strioglactone, (−)-solanocol, is described.

Synthesis of naturally occurring o-heterocyclic compounds of biological activity

2004 ◽  
Vol 76 (5) ◽  
pp. 1025-1032 ◽  
Author(s):  
Sándor Antus ◽  
Katalin Gulácsi ◽  
László Juhász ◽  
Loránd Kiss ◽  
Tibor Kurtán
Keyword(s):  
Biological Activity ◽  
Circular Dichroism ◽  
Total Synthesis ◽  
Heterocyclic Compounds ◽  
Optical Resolution ◽  
Enantioselective Synthesis ◽  
Ring Closure ◽  
X Ray ◽  
Naturally Occurring ◽  
Circular Dichroïsm

The total synthesis of (−)-cabenegrin A-I was achieved via (−)-6aR,11aR maackiain, which was obtained by optical resolution of racemic maackiain using S-(−)-alpha-methylbenzyl isocyanate. The synthesis of rac-maackiain was performed both with the Heck oxyarylation of 7-benzyloxy-2H-chromene and the BF3OEt2 mediated ring closure of isoflavan-4-ol derivatives, the latter of which provided much higher yields. The first enantioselective synthesis of trans-6aS,11aR-pterocarpan and its conversion to cis-6aS,11aS -ptarocarpan was also presented starting from racemic 2'-benzyloxyflavanone. Their stereochemistry was deduced by circular dichroism (CD) as well as by X-ray analysis of the ketal intermediate.

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
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