Short synthesis of phenylpropanoid glycosides calceolarioside A and syringalide B
An efficient and practical three-step synthesis of phenylpropanoid glycosides calceolarioside A and syringalide B in >62% overall yield is disclosed. The key step involves the chemoselective and regio selective direct O-4 cinnamoylation of unprotected 2-phenylethyl-β-d-glucosides with cinnamic an...
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sg-ntu-dr.10356-1389982020-05-14T09:11:21Z Short synthesis of phenylpropanoid glycosides calceolarioside A and syringalide B Khong, Duc Thinh Judeh, Zaher M. A. School of Chemical and Biomedical Engineering Engineering::Bioengineering Phenylpropanoid Glycosides Phenylethanoid Glycosides An efficient and practical three-step synthesis of phenylpropanoid glycosides calceolarioside A and syringalide B in >62% overall yield is disclosed. The key step involves the chemoselective and regio selective direct O-4 cinnamoylation of unprotected 2-phenylethyl-β-d-glucosides with cinnamic anhydrides using a chiral 4-pyrrolidinopyridine organocatalyst. This approach serves as a model for the short synthesis of phenylpropanoid glycosides acylated at O-4 without protection/deprotection steps. 2020-05-14T09:11:21Z 2020-05-14T09:11:21Z 2018 Journal Article Khong, D. T., & Judeh, Z. M. A. (2018). Short synthesis of phenylpropanoid glycosides calceolarioside A and syringalide B. Synlett, 29(8), 1079-1083. doi:10.1055/s-0036-1591753 0936-5214 https://hdl.handle.net/10356/138998 10.1055/s-0036-1591753 2-s2.0-85041636655 8 29 1079 1083 en Synlett © 2018 Georg Thieme Verlag Stuttgart·New York. All rights reserved. This paper was published in Synlett and is made available with permission of Georg Thieme Verlag Stuttgart·New York. |
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Nanyang Technological University |
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Singapore |
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| language |
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| topic |
Engineering::Bioengineering Phenylpropanoid Glycosides Phenylethanoid Glycosides |
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Engineering::Bioengineering Phenylpropanoid Glycosides Phenylethanoid Glycosides Khong, Duc Thinh Judeh, Zaher M. A. Short synthesis of phenylpropanoid glycosides calceolarioside A and syringalide B |
| description |
An efficient and practical three-step synthesis of phenylpropanoid glycosides calceolarioside A and syringalide B in >62% overall yield is disclosed. The key step involves the chemoselective and regio selective direct O-4 cinnamoylation of unprotected 2-phenylethyl-β-d-glucosides with cinnamic anhydrides using a chiral 4-pyrrolidinopyridine organocatalyst. This approach serves as a model for the short synthesis of phenylpropanoid glycosides acylated at O-4 without protection/deprotection steps. |
| author2 |
School of Chemical and Biomedical Engineering |
| author_facet |
School of Chemical and Biomedical Engineering Khong, Duc Thinh Judeh, Zaher M. A. |
| format |
Article |
| author |
Khong, Duc Thinh Judeh, Zaher M. A. |
| author_sort |
Khong, Duc Thinh |
| title |
Short synthesis of phenylpropanoid glycosides calceolarioside A and syringalide B |
| title_short |
Short synthesis of phenylpropanoid glycosides calceolarioside A and syringalide B |
| title_full |
Short synthesis of phenylpropanoid glycosides calceolarioside A and syringalide B |
| title_fullStr |
Short synthesis of phenylpropanoid glycosides calceolarioside A and syringalide B |
| title_full_unstemmed |
Short synthesis of phenylpropanoid glycosides calceolarioside A and syringalide B |
| title_sort |
short synthesis of phenylpropanoid glycosides calceolarioside a and syringalide b |
| publishDate |
2020 |
| url |
https://hdl.handle.net/10356/138998 |
| _version_ |
1681056182250242048 |