ChemInform Abstract: NATURALLY OCCURRING TEN-MEMBERED LACTONES: TOTAL SYNTHESIS OF (.+-.)-DIPLODIALIDE A, (.+-.)-DIPLODIALIDE C, AND (.+-.)-DECAN-9-OLIDE

1979 ◽  
Vol 10 (43) ◽  
Author(s):  
T. WAKAMATSU ◽  
K. AKASAKA ◽  
Y. BAN
Keyword(s):  
Total Synthesis ◽  
Naturally Occurring

scholarly journals Oxazolidinones as Chiral Auxiliaries in the Asymmetric 1,4-Conjugate Addition Reaction Applied to the Total Synthesis of Natural Products: A Supplemental Mini-Review

2018 ◽  
Vol 15 (1) ◽  
pp. 3-20 ◽  
Author(s):  
Vahideh Zadsirjan ◽  
Majid M. Heravi
Keyword(s):  
Total Synthesis ◽  
Biological Activities ◽  
Conjugate Addition ◽  
Chiral Auxiliary ◽  
Addition Reactions ◽  
Chiral Auxiliaries ◽  
Complex Molecules ◽  
Total Syntheses ◽  
Naturally Occurring ◽  
Wide Range

Background: The most frequently used chiral auxiliaries, oxazolidinones (Evans' oxazolidinones) have been employed in 1,4-congugate addition reactions to α,β-unsaturated carbonyl compounds. Supplementary to our previous reports in this mini-review, we attempted to underscore the applications of this strategy in a step (steps) in the total synthesis of some naturally occurring compounds exhibiting diverse biological activities. Objective: In this mini-review, we try to underscore the applications of oxazolidinones (Evans’ oxazolidinones) in 1,4-congugate addition reactions to α,β-unsaturated carbonyl in the total synthesis of some naturally occurring compounds exhibiting diverse biological activities. Conclusion: In spite of well-known superiority of asymmetric catalyzed reactions, the use of auxiliarycontrolled reactions are still considered as commanding, vital and sometimes as only tools in the generation of stereogenic centers during the construction of complex molecules and total synthesis of naturally occurring compounds. The commercial availability, or readily accessibility of a wide variety of chiral amino alcohols as starting materials to synthesize a wide range of oxazolidinones is the merits of them. In addition, the ease of removal and subjection to various and diverse stereoselective reactions make oxazolidinones as the ideal and superior chiral auxiliaries. In this regard, they were successfully used in asymmetric 1,4-conjugate addition reactions with high stereoselectivities. The high degree of asymmetric induction can be attributed to the rigid chelation of N-acyloxazolidinones with metal ions, as well as the covering of one face of the system by the bulkiness of 4-substituent. In summary, in this report, the importance of the applications of chiral oxazolidinones as suitable chiral auxiliaries in the stereoselective, 1,4-conjugate addition reactions in asymmetric synthesis and in particular, the total synthesis of naturally occurring compounds and some complex molecules were underscored. Noticeably, in these total syntheses, this chiral auxiliary is controlling the stereochemistry of a newly created stereogenic center as well as preserving the configuration of other chiral centers, which already have been presented in the precursor. General methods have been established for the attachment of the chiral auxiliary as a moiety to the substrate molecule in high to excellent yields. At the end of these reactions, this auxiliary can be easily removed leaving various desired reactive motifs for the next step in multi-step synthesis.

ChemInform Abstract: Total Synthesis and Determination of the Absolute Configuration of FD-838, a Naturally Occurring Azaspirobicyclic Product.

ChemInform ◽  
2009 ◽  
Vol 40 (47) ◽  
Author(s):  
Yujiro Hayashi ◽  
Kuppusamy Sankar ◽  
Hayato Ishikawa ◽  
Yuriko Nozawa ◽  
Kazutoshi Mizoue ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Absolute Configuration ◽  
Naturally Occurring ◽  
The Absolute

First total synthesis of a naturally occurring nucleoside disulfide: 9-(5′-Deoxy-5′-thio-β-d-xylofuranosyl)adenine disulfide

2012 ◽  
Vol 23 (9) ◽  
pp. 996-998 ◽  
Author(s):  
Hai Xin Ding ◽  
Ling Cui Da ◽  
Ru Chun Yang ◽  
Ban Peng Cao ◽  
Qi Sun ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Naturally Occurring

First total synthesis of cryptopyranmoscatone A2 from d-ribose

RSC Advances ◽  
2015 ◽  
Vol 5 (45) ◽  
pp. 35746-35752 ◽  
Author(s):  
A. Maheswara Reddy ◽  
Gowravaram Sabitha ◽  
Sirisha katukuri
Keyword(s):  
Total Synthesis ◽  
Naturally Occurring

The first total synthesis of a naturally occurring styryl lactone, cryptopyranmoscatone A2 has been achieved from inexpensive and highly abundant d-ribose.

scholarly journals Synthesis of ribosyl-ribosyl-adenosine-5′,5′′,5′′′(triphosphate)—the naturally occurring branched fragment of poly(ADP ribose)

2017 ◽  
Vol 53 (74) ◽  
pp. 10255-10258 ◽  
Author(s):  
Qiang Liu ◽  
Hans. A. V. Kistemaker ◽  
Herman S. Overkleeft ◽  
Gijsbert A. van der Marel ◽  
Dmitri V. Filippov
Keyword(s):  
Total Synthesis ◽  
Chemical Structure ◽  
Naturally Occurring ◽  
Branching Point ◽  
Independent Confirmation

Total synthesis provided the first independent confirmation of the chemical structure of the branching point in poly(ADP ribose).

scholarly journals Crocetin: A Systematic Review

2022 ◽  
Vol 12 ◽  
Author(s):  
Zi-Liang Guo ◽  
Mao-Xing Li ◽  
Xiao-Lin Li ◽  
Peng Wang ◽  
Wei-Gang Wang ◽  
...  
Keyword(s):  
Systematic Review ◽  
Medicinal Plants ◽  
Total Synthesis ◽  
Drug Safety ◽  
Ripe Fruit ◽  
Bioactive Metabolite ◽  
Naturally Occurring ◽  
Hydrolysis Of ◽  
Application Prospects ◽  
Memory Enhancing

Crocetin is an aglycone of crocin naturally occurring in saffron and produced in biological systems by hydrolysis of crocin as a bioactive metabolite. It is known to exist in several medicinal plants, the desiccative ripe fruit of the cape jasmine belonging to the Rubiaceae family, and stigmas of the saffron plant of the Iridaceae family. According to modern pharmacological investigations, crocetin possesses cardioprotective, hepatoprotective, neuroprotective, antidepressant, antiviral, anticancer, atherosclerotic, antidiabetic, and memory-enhancing properties. Although poor bioavailability hinders therapeutic applications, derivatization and formulation preparation technologies have broadened the application prospects for crocetin. To promote the research and development of crocetin, we summarized the distribution, preparation and production, total synthesis and derivatization technology, pharmacological activity, pharmacokinetics, drug safety, drug formulations, and preparation of crocetin.

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