Conversion of (−)-3-Dehydroshikimic Acid into Derivatives of the (+)-Enantiomer

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

doi:10.1021/jo034689c

Cited by 12 publications

(11 citation statements)

References 16 publications

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“…The use of diisobutylaluminium hydride (DIBAL-H) [30] as reducing agent on the other hand gave alcohol 24b suitable for the synthesis of non-natural 4a-epi-altenuene as a single isomer in an excellent 98 % yield. K-Selectride, which has proven successful in similar transformations, [31] led to significant over-reduction when applied to iodo enone 23.…”

Section: Resultsmentioning

confidence: 99%

Total Synthesis of Neoaltenuene

Altemöller

Podlech

2009

Eur J Org Chem

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Section: Resultsmentioning

confidence: 99%

Total Synthesis of Neoaltenuene

Altemöller

Podlech

2009

Eur J Org Chem

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“…In doing so, we have developed syntheses of the homochiral γ‐hydroxycyclohexenone 194 and its enantiomer from D ‐(−)‐ and L ‐(+)‐tartaric acid, respectively, and used the former chiron to prepare the cyclic carbonate‐containing natural product aspergillusol B ( 195 ) . We have also exploited the now abundant metabolite (−)‐3‐dehydroshikimic acid ( 196 ) in the development of a synthesis of the sialic acid (−)‐KDN ( 197 ) and also established simple protocols for converting it into its enantiomer 198 . With the assistance of colleagues in the biotech industry we have also produced new cis ‐1,2‐dihydrocatechols such as 199 as well as beginning to explore the chemistry of levoglucosenone ( 200 ), a material that is now available in tonne quantities through pyrolysis of acid‐impregnated waste paper and other cellulosic materials.…”

Section: New Chironsmentioning

confidence: 99%

The Exploitation of Enzymatically‐Derived cis‐1,2‐Dihydrocatechols and Related Compounds in the Synthesis of Biologically Active Natural Products

Taher

Banwell

Buckler

et al. 2017

The Chemical Record

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The title compounds of the general form 1 can be produced at large scale and in essentially enantiomerically pure form (when X≠H) through the whole cell biotransformation of the corresponding aromatic. The "dense" and varied functionality associated with these metabolites mean that they have become increasingly useful chirons for the total synthesis of a range of natural product types. This personal account details the outcomes of a nearly three-decade long campaign within our group to exploit these compounds in the synthesis of a diverse range of small molecule natural product targets. The work is subdivided according to the key transformation(s) employed in each synthesis. The development of newer chirons that "complement" the utility of the cis-1,2-dihydrocatechols are also described.

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“…Banwell et al . reported a synthesis of methyl ester of ent ‐ 2 from (−)‐quinic acid in 2003 [35] . Gotor et al .…”

Section: Resultsmentioning

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

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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.

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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.

Cited by 12 publications

References 16 publications

Total Synthesis of Neoaltenuene

Total Synthesis of Neoaltenuene

The Exploitation of Enzymatically‐Derived cis‐1,2‐Dihydrocatechols and Related Compounds in the Synthesis of Biologically Active Natural Products

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

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