Conversion of (-)-3-dehydroshikimic acid into derivatives of the (+)-enantiomer

Martin G. Banwell; Alison J. Edwards; Michael Essers; Katrina A. Jolliffe

doi:10.1021/jo034689c

Conversion of (-)-3-dehydroshikimic acid into derivatives of the (+)-enantiomer

Martin G. Banwell^*, Alison J. Edwards, Michael Essers, Katrina A. Jolliffe

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

13 Citations (Scopus)

Abstract

(-)-3-DHS (1), a compound available in large quantity through "engineering" of the shikimic acid pathway, has been converted over eight steps into the methyl ester, ent-2, of the (+)-enantiomer. Methyl (+)-shikimate (15) and its C-3 epimer (ent-5) have also been prepared by related means.

Original language	English
Pages (from-to)	6839-6841
Number of pages	3
Journal	Journal of Organic Chemistry
Volume	68
Issue number	17
DOIs	https://doi.org/10.1021/jo034689c
Publication status	Published - 1 Sept 2003

Access to Document

10.1021/jo034689c

Cite this

@article{7a5cf9e4be9448c0b35a66ad05223882,

title = "Conversion of (-)-3-dehydroshikimic acid into derivatives of the (+)-enantiomer",

abstract = "(-)-3-DHS (1), a compound available in large quantity through {"}engineering{"} of the shikimic acid pathway, has been converted over eight steps into the methyl ester, ent-2, of the (+)-enantiomer. Methyl (+)-shikimate (15) and its C-3 epimer (ent-5) have also been prepared by related means.",

author = "Banwell, {Martin G.} and Edwards, {Alison J.} and Michael Essers and Jolliffe, {Katrina A.}",

year = "2003",

month = sep,

day = "1",

doi = "10.1021/jo034689c",

language = "English",

volume = "68",

pages = "6839--6841",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "17",

}

TY - JOUR

T1 - Conversion of (-)-3-dehydroshikimic acid into derivatives of the (+)-enantiomer

AU - Banwell, Martin G.

AU - Edwards, Alison J.

AU - Essers, Michael

AU - Jolliffe, Katrina A.

PY - 2003/9/1

Y1 - 2003/9/1

N2 - (-)-3-DHS (1), a compound available in large quantity through "engineering" of the shikimic acid pathway, has been converted over eight steps into the methyl ester, ent-2, of the (+)-enantiomer. Methyl (+)-shikimate (15) and its C-3 epimer (ent-5) have also been prepared by related means.

AB - (-)-3-DHS (1), a compound available in large quantity through "engineering" of the shikimic acid pathway, has been converted over eight steps into the methyl ester, ent-2, of the (+)-enantiomer. Methyl (+)-shikimate (15) and its C-3 epimer (ent-5) have also been prepared by related means.

UR - http://www.scopus.com/inward/record.url?scp=0042890560&partnerID=8YFLogxK

U2 - 10.1021/jo034689c

DO - 10.1021/jo034689c

M3 - Article

SN - 0022-3263

VL - 68

SP - 6839

EP - 6841

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 17

ER -

Conversion of (-)-3-dehydroshikimic acid into derivatives of the (+)-enantiomer

Abstract

Access to Document

Other files and links

Fingerprint

Cite this