Novel stereoselective syntheses of N-octyl-β-valienamine (NOV) and N-octyl-4-epi-β-valienamine (NOEV) from (−)-shikimic acid

Li, Fenglei; Yu, Jiang-Ping; Ding, Wei; Sun, Mian-Mian; He, Yun-Gang; Zhu, Xingliang; Liu, Shi-Ling

doi:10.1039/c9ra09235h

Cited by 3 publications

(3 citation statements)

References 57 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Recently, Li et al 91 ) reported an efficient synthesis of 26 and 27 from naturally abundant shikimic acid with overall yields of 31% (14 steps) and 19% (17 steps), respectively.…”

Section: Development Of Carbaglycosylamine-based Pharmacological Chap...mentioning

confidence: 99%

“…Debenzoylation of the mixture in basic conditions led to the formation of the ,bromide 166 and the ,-epoxide 167 in 47% and 26% yield, respectively. Because the subsequent coupling reaction of 166 and 167 with n-octylamine yielded the same product,89) the mixture of 166 and 167, without isolation, was treated with n-octylamine followed by deisopropylidenation to give 27 as the sole product in 47% yield.Recently, Li et al91) reported an efficient synthesis of 26 and 27 from naturally abundant shikimic acid with overall yields of 31% (14 steps) and 19% (17 steps), respectively.…”

mentioning

confidence: 99%

See 1 more Smart Citation

Design and synthesis of biologically active carbaglycosylamines: From glycosidase inhibitors to pharmacological chaperones

Ogawa

Kuno

Toyokuni

2022

Proceedings of the Japan Academy. Ser. B: Physical and Biologic

View full text Add to dashboard Cite

For over 50 years, our group has been involved in synthetic studies on biologically active cyclitols including carbasugars. Among a variety of compounds synthesized, this review focuses on carbaglycosylamine glycosidase inhibitors, highlighting the following: (1) the naturally occurring N -linked carbaoligosaccharide α-amylase inhibitor acarbose and related compounds; (2) the novel synthetic β-glycosidase inhibitors, 1′- epi -acarviosin and its 6-hydroxy analogue as well as β-valienaminylceramide and its 4′-epimer; (3) the discovery of the β-glycosidase inhibitors with chaperone activity, N -octyl-β-valienamine (NOV) and its 4-epimer (NOEV); and (4) the recent development of the potential pharmacological chaperone N -alkyl-conduramine F-4 derivatives.

show abstract

“…Recently, Li et al 91 ) reported an efficient synthesis of 26 and 27 from naturally abundant shikimic acid with overall yields of 31% (14 steps) and 19% (17 steps), respectively.…”

Section: Development Of Carbaglycosylamine-based Pharmacological Chap...mentioning

confidence: 99%

mentioning

confidence: 99%

Design and synthesis of biologically active carbaglycosylamines: From glycosidase inhibitors to pharmacological chaperones

Ogawa

Kuno

Toyokuni

2022

Proceedings of the Japan Academy. Ser. B: Physical and Biologic

View full text Add to dashboard Cite

show abstract

“…(−)‐SA 1 is very useful material for syntheses of drugs and pharmaceutically valuable natural products. For examples, it has been extensively used in the syntheses of oseltamivir phosphate (Tamiflu), [7] valiolamine, [8] valienamine, [8a,9] NOV, [10] NOEV, [10] pericosines (A, B, D and E), [11] zeylenones, [12] (−)‐MK7607, [13] previtamin D 3 , [14] quercitols, [15] and (−)‐quinic acid [16] . (−)‐SA 1 and its derivatives might also be very important in drug discovery, since they have shown a wide range of physiological activities [17] such as antiviral, anti‐bacterial, anti‐fungi, anti‐osteoclastogenesis, anti‐platelet, anti‐thrombogenic, anti‐inflammatory, anti‐oxidant, and anti‐tumor activities.…”

Section: Introductionmentioning

confidence: 99%

Stereodivergent Syntheses of All Stereoisomers of (−)‐Shikimic Acid: Development of a Chiral Pool for the Diverse Polyhydroxy‐cyclohexenoid (or ‐cyclohexanoid) Bioactive Molecules

Huang

et al. 2021

Eur J Org Chem

Self Cite

View full text Add to dashboard Cite

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.

show abstract

Novel Stereoselective Syntheses of (+)-Streptol and (−)-1-epi-Streptol Starting from Naturally Abundant (−)-Shikimic Acid

et al. 2021

Self Cite

View full text Add to dashboard Cite

Novel highly stereoselective syntheses of (+)-streptol and (−)-1-epi-streptol starting from naturally abundant (−)-shikimic acid were described in this article. (−)-Shikimic acid was first converted to the common key intermediate by 11 steps in 40% yield. It was then converted to (+)-streptol by three steps in 72% yield, and it was also converted to (−)-1-epi-streptol by one step in 90% yield. In summary, (+)-streptol and (−)-1-epi-streptol were synthesized from (−)-shikimic acid by 14 and 12 steps in 29 and 36% overall yields, respectively.

show abstract

Novel stereoselective syntheses of N-octyl-β-valienamine (NOV) and N-octyl-4-epi-β-valienamine (NOEV) from (−)-shikimic acid

Abstract: Novel stereoselective syntheses of N-octyl-β-valienamine (NOV) 1 and N-octyl-4-epi-β-valienamine (NOEV) 2 starting from naturally abundant (−)-shikimic acid are described in this article.

Cited by 3 publications

References 57 publications

Design and synthesis of biologically active carbaglycosylamines: From glycosidase inhibitors to pharmacological chaperones

Design and synthesis of biologically active carbaglycosylamines: From glycosidase inhibitors to pharmacological chaperones

Stereodivergent Syntheses of All Stereoisomers of (−)‐Shikimic Acid: Development of a Chiral Pool for the Diverse Polyhydroxy‐cyclohexenoid (or ‐cyclohexanoid) Bioactive Molecules

Novel Stereoselective Syntheses of (+)-Streptol and (−)-1-epi-Streptol Starting from Naturally Abundant (−)-Shikimic Acid

Contact Info

Product

Resources

About