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

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.

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.

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

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.

Facile synthesis of the enantiomers of frontalin

1984 ◽  
Vol 62 (11) ◽  
pp. 2148-2154 ◽  
Author(s):  
B. D. Johnston ◽  
A. C. Oehlschlager
Keyword(s):  
Asymmetric Epoxidation ◽  
Facile Synthesis ◽  
Epoxidation Reaction ◽  
Synthetic Sequence ◽  
Sharpless Asymmetric Epoxidation

S-(−)- and R-(+)-frontalin (1,5-dimethyl-6,8-dioxabicyclo[3.2.1]octane) were prepared from (E)-2-methyl-2,6-heptadiene-1-ol utilizing the Sharpless asymmetric epoxidation reaction to induce chirality. The six-step synthetic sequence proceeded in approximately 50% overall yield and was found to be suitable for the preparation of multi-gram quantities of either enantiomer with ≥ 90% ee.

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