Limits...
Total synthesis of the putative structure of the proposed Banyasin A.

Gao X, Ren Q, Choi S, Xu Z, Ye T - Front Chem (2015)

Bottom Line: The first total synthesis of four possible isomers of a molecule possessing the configuration proposed for Banyasin A is described.The structure synthesized appears to be different from that of the natural product.

View Article: PubMed Central - PubMed

Affiliation: Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School Shenzhen, China.

ABSTRACT
The first total synthesis of four possible isomers of a molecule possessing the configuration proposed for Banyasin A is described. The structure synthesized appears to be different from that of the natural product.

No MeSH data available.


Comparison of 1H NMR of natural and synthetic banyasin A (1a–d).
© Copyright Policy - open-access
Related In: Results  -  Collection

License
getmorefigures.php?uid=PMC4362330&req=5

Figure 8: Comparison of 1H NMR of natural and synthetic banyasin A (1a–d).

Mentions: We have developed a convergent route for the synthesis of the proposed structure of banyasin A. The optical rotation measured for synthetic banyasin A 1a–d ([α]20D = −45.6 (c = 0.70, MeOH); [α]20D = −59.4 (c = 0.70, MeOH); [α]20D = −37.3 (c = 0.70, MeOH); and [α]20D = −53.1 (c = 0.70, MeOH); were identical or nearly identical to that reported for the natural product [α]20D = −45.3 (c = 0.7, MeOH). To our disappointment, both the 1H and 13C spectroscopic properties of each diastereomer 1a, 1b, 1c, and 1d were different from those of banyasin A (Figure 8 and Supplementary Material). It would appear that the error in the original assignment of the configuration of banyasin A lies somewhere in the remaining α-aminoacids. The extension of this chemistry toward the synthesis of additional diastereomers aiming to resolve the true structure of natural banyasin A and synthesis of novel analogs of banyasin for biological evaluation are underway in our laboratory.


Total synthesis of the putative structure of the proposed Banyasin A.

Gao X, Ren Q, Choi S, Xu Z, Ye T - Front Chem (2015)

Comparison of 1H NMR of natural and synthetic banyasin A (1a–d).
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4362330&req=5

Figure 8: Comparison of 1H NMR of natural and synthetic banyasin A (1a–d).
Mentions: We have developed a convergent route for the synthesis of the proposed structure of banyasin A. The optical rotation measured for synthetic banyasin A 1a–d ([α]20D = −45.6 (c = 0.70, MeOH); [α]20D = −59.4 (c = 0.70, MeOH); [α]20D = −37.3 (c = 0.70, MeOH); and [α]20D = −53.1 (c = 0.70, MeOH); were identical or nearly identical to that reported for the natural product [α]20D = −45.3 (c = 0.7, MeOH). To our disappointment, both the 1H and 13C spectroscopic properties of each diastereomer 1a, 1b, 1c, and 1d were different from those of banyasin A (Figure 8 and Supplementary Material). It would appear that the error in the original assignment of the configuration of banyasin A lies somewhere in the remaining α-aminoacids. The extension of this chemistry toward the synthesis of additional diastereomers aiming to resolve the true structure of natural banyasin A and synthesis of novel analogs of banyasin for biological evaluation are underway in our laboratory.

Bottom Line: The first total synthesis of four possible isomers of a molecule possessing the configuration proposed for Banyasin A is described.The structure synthesized appears to be different from that of the natural product.

View Article: PubMed Central - PubMed

Affiliation: Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School Shenzhen, China.

ABSTRACT
The first total synthesis of four possible isomers of a molecule possessing the configuration proposed for Banyasin A is described. The structure synthesized appears to be different from that of the natural product.

No MeSH data available.