15271-51-9Relevant academic research and scientific papers
A C 2-symmetric chiral pool-based flexible strategy: Synthesis of (+)- and (-)-shikimic acids, (+)- and (-)-4- epi -shikimic acids, and (+)- and (-)-pinitol
Ananthan, Bakthavachalam,Chang, Wan-Chun,Lin, Jhe-Sain,Li, Pin-Hui,Yan, Tu-Hsin
, p. 2898 - 2905 (2014)
Via combination of a novel acid-promoted rearrangement of acetal functionality with the controlled installation of the epoxide unit to create the pivotal epoxide intermediates in enantiomerically pure form, a simple, concise, flexible, and readily scalable enantiodivergent synthesis of (+)- and (-)-shikimic acids and (+)- and (-)-4-epi-shikimic acids has emerged. This simple strategy not only provides an efficient approach to shikimic acids but also can readily be adopted for the synthesis of (+)- and (-)-pinitols. These concise total syntheses exemplify the use of pivotal allylic epoxide 14 and its enantiomer ent-14. A readily available inexpensive C2-symmetric l-tartaric acid (7) served as key precursor. In general, the strategy here provides a neat example of the use of a four-carbon chiron and offers a good account of the synthesis of functionalized cyclohexane targets.
Stereodivergent Syntheses of All Stereoisomers of (?)-Shikimic Acid: Development of a Chiral Pool for the Diverse Polyhydroxy-cyclohexenoid (or -cyclohexanoid) Bioactive Molecules
He, Yun-Gang,Huang, Yong-Kang,Xu, Zhang-Li,Xie, Wen-Jing,Luo, Yong-Qiang,Li, Feng-Lei,Zhu, Xing-Liang,Shi, Xiao-Xin
, p. 4318 - 4332 (2021/07/21)
Novel stereodivergent total syntheses of all the seven stereoisomers of (?)-shikimic acid [(?)-SA 1] have been systematically performed. (+)-ent-SA ent-1 was synthesized from (?)-SA 1 via 9 steps in 31 % overall yield; (?)-3-epi-SA 2 was synthesized from (?)-SA 1 via 5 steps in 66 % overall yield; (+)-3-epi-ent-SA ent-2 was synthesized from (?)-SA 1 via 7 steps in 43 % overall yield; (?)-4-epi-SA 3 was synthesized from (?)-SA 1 via 11 steps in 32 % overall yield; (+)-4-epi-ent-SA ent-3 was synthesized from (?)-SA 1 via 7 steps in 42 % overall yield; (?)-5-epi-SA 4 was synthesized from (?)-SA 1 via 6 steps in 56 % overall yield; and (+)-5-epi-ent-SA ent-4 was synthesized from (?)-SA 1 via 12 steps in 29 % overall yield. The stereochemistry of all the above seven stereoisomers of (?)-SA 1 were further studied by two dimensional (2D) 1H NMR technique.
(1E,3E)-4-acetoxy-1-phenyldimethylsilyl-1,3-butadiene as a surrogate for (1E,3E)-1,4-diacetoxy-1,3-butadiene: A highly coefficient synthesis of (±)-shikimic acid
Koreeda,Teng,Murata
, p. 5997 - 6000 (2007/10/02)
The 5-step synthesis of (±)-shikimic acid has been achieved in 55% overall yield from (1E,3E)-4-acetoxy-1-phenyldimethylsilyl-1,3-butadiene, starting with its Diels-Alder reaction with 2-(trimethylsilyl)ethyl acrylate and featuring the use of Fleming's on
SHIKIMIC ACIDS FROM FURAN; METHODS OF STEREOCONTROLLED ACCESS TO 3,4,5-TRIOXIGENATED CYCLOHEXENES
Rajapaksa, D.,Keay, B. A.,Rodrigo, R.
, p. 826 - 828 (2007/10/02)
Oxabicycloheptenes 1 and 2 are converted to 3,4,5-oxigenated cyclohexenes by stereocontrolled hydroxylations and epoxidations coupled with reverse-Michael cleavage of the oxabicyclo system.Three epimers of shikimic acid are synthesized by these methods.
Shikimate-Derived Metabolites. 12. Stereocontrolled Total Synthesis of Shikimic Acid and 6β-Deuterioshikimate
Coblens, Karen E.,Muralidharan, V. B.,Ganem, Bruce
, p. 5041 - 5042 (2007/10/02)
A short total synthesis of shikimic acid and related derivatives is described in which an unusual, stereoselective Bu3SnD debromination conveniently furnishes 6β-deuterioshikimate for biosynthetic studies.
