First Total Synthesis of Jomthonic Acid A

Synlett ◽  
2019 ◽  
Vol 31 (01) ◽  
pp. 69-72
Author(s):  
Mohan Dumpala ◽  
Batthula Srinivas ◽  
Palakodety Radha Krishna
Keyword(s):  
Amino Acid ◽  
Total Synthesis ◽  
Mitsunobu Reaction ◽  
Asymmetric Epoxidation ◽  
Synthetic Strategy ◽  
Amide Coupling ◽  
Key Features ◽  
Sharpless Asymmetric Epoxidation

A stereoselective total synthesis of jomthonic acid A is described. The key features of the synthetic strategy are a Sharpless asymmetric epoxidation, a Gilmann reagent-induced methylation, a Mitsunobu reaction, a Yamaguchi esterification, and an O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (TBTU)-mediated amide coupling. Jomthonic acid A is an architecturally rare amino acid containing a β-methylphenylalanine residue and a 4-methyl-(2E,4E)-hexa-2,4-dienoate moiety. It shows antidiabetic and antiatherogenic activities when tested against mouse ST-13 preadiopocytes.

Stereo-Controlled Total Synthesis of Ieodomycins A and B

2014 ◽  
Vol 881-883 ◽  
pp. 57-60 ◽  
Author(s):  
Cheng Lin Zhu ◽  
Jian Ting Zhang ◽  
Shi Peng Chen ◽  
Jun Min Feng ◽  
Gao Peng Wang ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Wittig Reaction ◽  
Aldol Reaction ◽  
Asymmetric Epoxidation ◽  
Formal Synthesis ◽  
Mukaiyama Aldol ◽  
Synthetic Sequence ◽  
Key Features ◽  
Swern Oxidation ◽  
Sharpless Asymmetric Epoxidation

A highly convergent formal synthesis of Ieodomycins A and B was achieved in 7 steps. The key features involved in the synthetic sequence of Ieodomycins A and B are the Sharpless asymmetric epoxidation and the Mukaiyama aldol reaction[. The synthesis of C-3 epimer of Ieodomycins A and B was also accomplished in good yields, but now just Heptyl diene aldehyde was getted thought 4 steps. Use Geraniol as meterials to make the corresponding aldehyde (1) via Swern oxidation. Though epoxidation, Wittig reaction and HIO4oxidation to get the intermediate . Useing it though few steps, the target molecule can be getted.

scholarly journals Synthesis of (–)-Kopsifoline A and (+)-Kopsifoline E

2021 ◽  
Author(s):  
In-Soo Myeong ◽  
Nadide Hazal Avci ◽  
Mohammad Movassaghi
Keyword(s):  
Total Synthesis ◽  
Bond Formation ◽  
Mitsunobu Reaction ◽  
Reaction Conditions ◽  
Synthetic Strategy ◽  
F Ring ◽  
Pentacyclic Core

We report the first total synthesis of (–)-kopsifoline A and (+)-kopsifoline E. Our synthetic strategy features a biogenetically inspired regioselective C17-functionalization of a versatile intermediate containing the pentacyclic core of aspidosperma alkaloids. While this advance intermediate provides (–)-kopsifoline D via C3–C21 bond formation, regioselective C17-boronation of its indoline substructure prior to introduction of the F-ring enables access to (–)-kopsifoline A and (+)-kopsifoline E. The vinylogous urethane substructure of the key intermediate was critical in C17-boronation over a competing C7-boronation in related indole derived substrates. After oxidation of the C17–B bond to introduce the C17-ether, the C3–C21 bond of the targets is secured under the Mitsunobu reaction conditions with the vinylogous urethane as the nucleophilic component.

A New Formal Synthetic Route to Entecavir

Synlett ◽  
2019 ◽  
Vol 30 (06) ◽  
pp. 748-752
Author(s):  
Xiaoji Wang ◽  
Shuangping Huang ◽  
Lixia Liu ◽  
Yongli Sun ◽  
Jiwu Wang ◽  
...  
Keyword(s):  
Hepatitis B ◽  
Selenium Dioxide ◽  
Asymmetric Epoxidation ◽  
Formal Synthesis ◽  
Virus Inhibitor ◽  
B Virus ◽  
Epoxide Opening ◽  
Key Features ◽  
Sharpless Asymmetric Epoxidation ◽  
Straightforward Approach

We describe a new and straightforward approach to the formal synthesis of the hepatitis B virus inhibitor entecavir, an important hepatitis B drug, in ten steps overall. Key features of the route are a Morita–Baylis–Hillman reaction, a Sharpless asymmetric epoxidation, a reductive epoxide opening of an α,β-epoxy ketone, and a Riley selenium dioxide oxidation.

scholarly journals Synthesis of the C8’-epimeric thymine pyranosyl amino acid core of amipurimycin

2016 ◽  
Vol 12 ◽  
pp. 1765-1771 ◽  
Author(s):  
Pramod R Markad ◽  
Navanath Kumbhar ◽  
Dilip D Dhavale
Keyword(s):  
Amino Acid ◽  
Allyl Alcohol ◽  
Ring Opening ◽  
Functional Group ◽  
Asymmetric Epoxidation ◽  
Oxirane Ring ◽  
Trimethyl Borate ◽  
Pyranose Ring ◽  
Acid Catalyzed ◽  
Sharpless Asymmetric Epoxidation

The C8’-epimeric pyranosyl amino acid core 2 of amipurimycin was synthesized from D-glucose derived alcohol 3 in 13 steps and 14% overall yield. Thus, the Sharpless asymmetric epoxidation of allyl alcohol 7 followed by trimethyl borate mediated regio-selective oxirane ring opening with azide, afforded azido diol 10. The acid-catalyzed 1,2-acetonide ring opening in 10 concomitantly led to the formation of the pyranose ring skeleton to give 2,7-dioxabicyclo[3.2.1]octane 12. Functional group manipulation in 12 gave 21 that on stereoselective β-glycosylation afforded the pyranosyl thymine nucleoside 2 – a core of amipurimycin.

scholarly journals Applications of Sharpless asymmetric epoxidation in total synthesis

2015 ◽  
Vol 26 (8-9) ◽  
pp. 405-495 ◽  
Author(s):  
Majid M. Heravi ◽  
Tahmineh Baie Lashaki ◽  
Nasim Poorahmad
Keyword(s):  
Total Synthesis ◽  
Asymmetric Epoxidation ◽  
Sharpless Asymmetric Epoxidation

scholarly journals A Facile Stereoselective Total Synthesis of (R)-Rugulactone

2014 ◽  
Vol 2014 ◽  
pp. 1-5 ◽  
Author(s):  
B. Narasimha Reddy ◽  
R. P. Singh
Keyword(s):  
Total Synthesis ◽  
Asymmetric Epoxidation ◽  
Cross Metathesis ◽  
Hydride Reduction ◽  
Novel Synthesis ◽  
Metathesis Reactions ◽  
Epoxy Alcohols ◽  
Allyl Alcohols ◽  
Sharpless Asymmetric Epoxidation

An efficient and novel synthesis of (R)-rugulactone has been achieved employing Sharpless asymmetric epoxidation of allyl alcohols followed by selective hydride reduction of epoxy alcohols and olefin cross metathesis reactions.

ChemInform Abstract: Applications of Sharpless Asymmetric Epoxidation in Total Synthesis

ChemInform ◽  
2015 ◽  
Vol 46 (25) ◽  
pp. no-no
Author(s):  
Majid M. Heravi ◽  
Tahmineh Baie Lashaki ◽  
Nasim Poorahmad
Keyword(s):  
Total Synthesis ◽  
Asymmetric Epoxidation ◽  
Sharpless Asymmetric Epoxidation

Total Synthesis of the Microtubule Stabilizing Antitumor Agent Laulimalide and Some Nonnatural Analogues:  The Power of Sharpless' Asymmetric Epoxidation

2003 ◽  
Vol 68 (8) ◽  
pp. 3026-3042 ◽  
Author(s):  
Anjum Ahmed ◽  
E. Kate Hoegenauer ◽  
Valentin S. Enev ◽  
Martin Hanbauer ◽  
Hanspeter Kaehlig ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Antitumor Agent ◽  
Asymmetric Epoxidation ◽  
Sharpless Asymmetric Epoxidation
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