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Synthesis of 2‐Fluoro Analogues of Frontalin - DeepDyve

Frontalin is an anti-aggregation pheromone of the Douglas Fir Bark Beetle (a northwest pest), and is manufactured by a company in Canada () for use against beetle attacks. (They actually called a couple years ago and were interested in any potential syntheses we come up with.) For more information on frontalin and its synthesis, I recommend the

SOPHIA - Scholar Week: Synthesis of Frontalin Pheromone
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A concise approach for the rapid synthesis of enantiomerically pure α-alkylated derivatives of lactate esters and of other enantiomerically pure α-hydroxy esters is presented. This methodology, which makes use of enantiomeric lithium enolates prepared from diastereomeric tetrahydropyranyl ethers derived from alkyl lactates and other α-hydroxy esters, is used to prepare both enantiomers of frontalin from (S)-(-)-methyl lactate.

Frontalin synthesis essay - Kidscool

We have been trying to develop an effective synthesis of frontalin for several years now.
Photo provided by Flickr

AB - A concise approach for the rapid synthesis of enantiomerically pure α-alkylated derivatives of lactate esters and of other enantiomerically pure α-hydroxy esters is presented. This methodology, which makes use of enantiomeric lithium enolates prepared from diastereomeric tetrahydropyranyl ethers derived from alkyl lactates and other α-hydroxy esters, is used to prepare both enantiomers of frontalin from (S)-(-)-methyl lactate.

Chelation-controlled asymmetric nucleophilic addition of a Grignard reagent to chiral α-benzyloxy ketones gives the corresponding alcohols with high diastereoselectivities (up to 96% de) by 1,4-asymmetric induction. A chiral benzyl group is used as a chiral auxiliary as well as a protecting group for the synthesis of optically active 1,2-diols and (+)-frontalin.

Protective group-free syntheses of (±)-frontalin, (±) …

SOPHIA - Scholar Week: Synthesis of Frontalin …
Photo provided by Flickr

We have been trying to develop an effective synthesis of frontalin for several years now, but none of the seemed to work out, so this year we are embarking on an entirely new approach inspired by the . (See also Trzoss, M.; Shao, J.; Bienz, S. 2002, , 5885-5894.)

Frontalin is an anti-aggregation pheromone of the Douglas Fir Bark Beetle (a northwest pest), and is manufactured by a company in Canada () for use against beetle attacks. (They actually called a couple years ago and were interested in any potential syntheses we come up with.) For more information on frontalin and its synthesis, I recommend the

Synthesis of frontalin, the aggregation phermone of …
Photo provided by Flickr
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New synthesis of both the enantiomers of frontalin - CORE

N2 - A concise approach for the rapid synthesis of enantiomerically pure α-alkylated derivatives of lactate esters and of other enantiomerically pure α-hydroxy esters is presented. This methodology, which makes use of enantiomeric lithium enolates prepared from diastereomeric tetrahydropyranyl ethers derived from alkyl lactates and other α-hydroxy esters, is used to prepare both enantiomers of frontalin from (S)-(-)-methyl lactate.

strategy for the synthesis of frontalin …

Chelation-controlled asymmetric nucleophilic addition of a Grignard reagent to chiral α-benzyloxy ketones gives the corresponding alcohols with high diastereoselectivities (up to 96% de) by 1,4-asymmetric induction. A chiral benzyl group is used as a chiral auxiliary as well as a protecting group for the synthesis of optically active 1,2-diols and (+)-frontalin.

methyl heptenone 110-93-0 - The Good Scents Company

We have been trying to develop an effective synthesis of frontalin for several years now. we tried an entirely new approach inspired by the . (See also Trzoss, M.; Shao, J.; Bienz, S. 2002, , 5885-5894.

Enantioselective Synthesis of Alcohols and Amines: The …

(+)-Endo-brevicomin is a male produced component of the attractive pheromone system of Dendroctonus frontalis (southern pine beetle),[] a tree-killing insect found in southern North America and Central America. It was envisioned that AROCM of 2 with 4-penten-2-ol would set the relative and absolute stereochemistry in the synthesis of (+)-endo brevicomin.

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