scholarly journals First Stereoselective Total Synthesis of Ciryneol C

SynOpen ◽  
2019 ◽  
Vol 03 (02) ◽  
pp. 59-66
Author(s):  
Ambati Sharada ◽  
Lakshmi Srinivasa Rao Kundeti ◽  
Kallaganti V. S. Ramakrishna ◽  
Kommu Nagaiah
Keyword(s):  
Total Synthesis ◽  
Coupling Reactions ◽  
Asymmetric Total Synthesis ◽  
Acetylene Derivative ◽  
Wittig Olefination ◽  
Epoxide Opening ◽  
Key Steps

The acetylene derivative Ciryneol C was isolated from the roots of C. japonicum. The asymmetric total synthesis of Ciryneol C was achieved in seven steps, with Horner–Wittig olefination, regioselective epoxide opening, and Cadiot–Chodkiewicz coupling reactions being the key steps.

scholarly journals Total syntheses of all tri-oxygenated 16-phytoprostane classes via a common precursor constructed by oxidative cyclization and alkyl–alkyl coupling reactions as the key steps

2017 ◽  
Vol 15 (44) ◽  
pp. 9408-9414 ◽  
Author(s):  
Jakub Smrček ◽  
Radek Pohl ◽  
Ullrich Jahn
Keyword(s):  
Total Synthesis ◽  
Oxidative Cyclization ◽  
Coupling Reactions ◽  
Total Syntheses ◽  
Common Precursor ◽  
Key Steps

A parallel total synthesis of 16-F1t-, 16-E1-phytoprostanes and a first synthesis of 16-D1t-phytoprostanes based on a common precursor are described.

Concise asymmetric total synthesis of bruceolline J

2015 ◽  
Vol 2 (5) ◽  
pp. 548-551 ◽  
Author(s):  
Dattatraya H. Dethe ◽  
Vijay Kumar B
Keyword(s):  
Total Synthesis ◽  
Lewis Acid ◽  
Asymmetric Total Synthesis ◽  
Asymmetric Dihydroxylation ◽  
Key Steps

Concise biomimetic and asymmetric approach involving Sharpless asymmetric dihydroxylation and Lewis acid catalysed cyclopenta[b]annulation as key steps to synthesize (+)-bruceolline J.

Asymmetric total synthesis of talienbisflavan A

2018 ◽  
Vol 16 (4) ◽  
pp. 585-592 ◽  
Author(s):  
Deng-Ming Huang ◽  
Hui-Jing Li ◽  
Jun-Hu Wang ◽  
Yan-Chao Wu
Keyword(s):  
Total Synthesis ◽  
Asymmetric Total Synthesis ◽  
Facile Synthesis ◽  
Total Syntheses ◽  
Key Steps

The first asymmetric total syntheses of talienbisflavan A and bis-8,8′-epicatechinylmethane as well as a facile synthesis of bis-8,8′-catechinylmethane has been accomplished from readily available starting materials by using a newly developed direct regioselective methylenation of catechin derivatives as one of the key steps.

scholarly journals Asymmetric total synthesis of a putative sex pheromone component from the parasitoid wasp Trichogramma turkestanica

2014 ◽  
Vol 10 ◽  
pp. 761-766 ◽  
Author(s):  
Danny Geerdink ◽  
Jeffrey Buter ◽  
Teris A van Beek ◽  
Adriaan J Minnaard
Keyword(s):  
Sex Pheromone ◽  
Total Synthesis ◽  
Parasitoid Wasp ◽  
Conjugate Addition ◽  
Enantioselective Synthesis ◽  
Pheromone Component ◽  
Asymmetric Total Synthesis ◽  
Catalytic Asymmetric ◽  
Key Steps

Virgin females of the parasitoid wasp Trichogramma turkestanica produce minute amounts of a sex pheromone, the identity of which has not been fully established. The enantioselective synthesis of a putative component of this pheromone, (6S,8S,10S)-4,6,8,10-tetramethyltrideca-2E,4E-dien-1-ol (2), is reported as a contribution to this identification. Catalytic asymmetric conjugate addition of methylmagnesium bromide and stereoselective Horner–Wadsworth–Emmons olefinations are used as the key steps, and 2 was obtained in 16 steps with an overall yield of 4.4%.

Asymmetric Total Synthesis of (+)-Brefeldin A: Intramolecular Epoxide-Opening/RCM Strategy

Synlett ◽  
2009 ◽  
Vol 2009 (08) ◽  
pp. 1303-1306 ◽  
Author(s):  
Jinsung Tae ◽  
Myung-Yeol Kim ◽  
Hyemi Kim
Keyword(s):  
Total Synthesis ◽  
Brefeldin A ◽  
Asymmetric Total Synthesis ◽  
Epoxide Opening

scholarly journals A catalytic asymmetric total synthesis of (−)-perophoramidine

2015 ◽  
Vol 6 (1) ◽  
pp. 349-353 ◽  
Author(s):  
B. M. Trost ◽  
M. Osipov ◽  
S. Krüger ◽  
Y. Zhang
Keyword(s):  
Total Synthesis ◽  
Allylic Alkylation ◽  
Asymmetric Total Synthesis ◽  
Asymmetric Allylic Alkylation ◽  
Catalytic Asymmetric ◽  
Key Steps

We describe a catalytic asymmetric total synthesis of the ascidian alkaloid (−)-perophoramidine employing a Mo-catalyzed asymmetric allylic alkylation and unprecedented imino ether allylation as key steps.

First Stereoselective Total Synthesis of Anti-Inflammatory Metabolite­ Penicillinolide A

Synthesis ◽  
2018 ◽  
Vol 51 (06) ◽  
pp. 1427-1434 ◽  
Author(s):  
Palakodety Krishna ◽  
Mopuri Reddy ◽  
Gembali Manikanta
Keyword(s):  
Total Synthesis ◽  
Kinetic Resolution ◽  
Asymmetric Allylation ◽  
Asymmetric Total Synthesis ◽  
Hydrolytic Kinetic Resolution ◽  
Anti Inflammatory ◽  
Key Steps

The first asymmetric total synthesis of penicillinolide A is described. Key steps of the synthesis involve Jacobsen’s hydrolytic kinetic resolution (HKR), chelation controlled allylation, Brown’s asymmetric allylation, hydroboration, and Yamaguchi lactonization.

scholarly journals A new phenylethyl alkyl amide from the Ambrostoma quadriimpressum Motschulsky

2011 ◽  
Vol 7 ◽  
pp. 1342-1346 ◽  
Author(s):  
Guolei Zhao ◽  
Chao Yang ◽  
Bing Li ◽  
Wujiong Xia
Keyword(s):  
Total Synthesis ◽  
Glutamic Acid ◽  
Absolute Configuration ◽  
Aliphatic Chain ◽  
Asymmetric Total Synthesis ◽  
Selective Protection ◽  
Wittig Olefination ◽  
The Absolute ◽  
Hydroxy Groups ◽  
Alkyl Amide

A new phenylethyl alkyl amide, (10R)-10-hydroxy-N-phenethyloctadecanamide (1), was isolated from the beetle Ambrostoma quadriimpressum Motschulsky. The structure of the amide was determined by NMR and MS. The absolute configuration of compound 1 was confirmed by an asymmetric total synthesis, which was started from L-glutamic acid. The construction of the aliphatic chain was accomplished by the selective protection of the hydroxy groups and two-time implementation of the Wittig olefination reaction.

Second-generation total synthesis of aplyronine A featuring Ni/Cr-mediated coupling reactions

2017 ◽  
Vol 15 (1) ◽  
pp. 124-131 ◽  
Author(s):  
Ichiro Hayakawa ◽  
Keita Saito ◽  
Sachiko Matsumoto ◽  
Shinichi Kobayashi ◽  
Ayaka Taniguchi ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Second Generation ◽  
Coupling Reactions ◽  
Key Steps ◽  
Aplyronine A

Second-generation total synthesis of aplyronine A, a potent antitumor marine macrolide, was achieved using Ni/Cr-mediated coupling reactions as key steps.

Total synthesis of (−)-depyranoversicolamide B

2015 ◽  
Vol 51 (89) ◽  
pp. 16143-16146 ◽  
Author(s):  
Wen-Fang Qin ◽  
T. Xiao ◽  
D. Zhang ◽  
Lin-Feng Deng ◽  
Y. Wang ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Ring Opening ◽  
Alder Reaction ◽  
Diels Alder ◽  
Asymmetric Total Synthesis ◽  
Diels Alder Reaction ◽  
Key Steps

Asymmetric total synthesis of (−)-depyranoversicolamide B (12) is described from easily prepared chiral pyrroloindoline 21. Key steps in the synthesis are reductive ring opening of the pyrrolo ring in 21 and stereoselective intramolecular Diels–Alder reaction of 18.

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