Enantiopure building blocks for the synthesis of 3-methyl-2-alkanols. Diastereoselective methylmetal addition to a chiral 2-methylaldehyde followed by lipase catalysed esterification

Larsson, Michael; Andersson, Jimmy; Liu, Rong; Högberg, Hans‐Erik

doi:10.1016/j.tetasy.2004.07.049

Cited by 8 publications

(2 citation statements)

References 38 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…However, in the past few years, researchers have found several pine sawfly species that use sex pheromones with structural types different from that of the diprionyl esters, including various stereoisomers of 3,7,11-trimethyltridecan-2-ol, 3,7-dimethyltridecan-2-ol, or 3,7-dimethylundecan-2-ol derivatives [84]. Indeed, several syntheses of both the actual sex pheromones of pine sawfly species [84][85][86] and their precursors [87][88][89][90] through lipasecatalyzed stereoselective acylation have been described.…”

Section: Synthesis Of Hydroxylated Phero-mones and Related Compoundsmentioning

confidence: 99%

Biocatalysis Applied to the Synthesis of Pheromones

Aleu¹,

Bustillo²,

Hernández-Galán³

et al. 2007

COC

View full text Add to dashboard Cite

The application of biologically derived catalysts to the synthesis of agrochemicals has become increasingly popular in recent years. In most cases, the aim of using a biotransformation is either to introduce chirality into the molecule, to achieve a regioselective functionalization, or to selectively convert a functional group among other groups with similar reactivity. Pheromones, which have recently been commercialized as agrochemicals, are generally used in enantiopure forms with their intentional mixtures. Since they are usually highly effective, only very small quantities are needed to achieve the desired activity. This review, with approximately 200 references covering the period previous to December 2004, describes various efficient means of preparing optically pure pheromones and their precursors with the aid of isolated enzymes and microorganisms serving as catalysts.

show abstract

Section: Synthesis Of Hydroxylated Phero-mones and Related Compoundsmentioning

confidence: 99%

Biocatalysis Applied to the Synthesis of Pheromones

Aleu¹,

Bustillo²,

Hernández-Galán³

et al. 2007

COC

View full text Add to dashboard Cite

show abstract

“…Surprisingly, Julia-type olefination employing sulfone derivatives of 7 were unreliable in providing the C17–C18 ( E )-alkene. Alternatively, the anion of phosphonium iodide 16 , prepared from 7 via iodide 15 , was coupled with the known aldehyde 8 under standard ( Z )-selective Wittig olefination conditions to give alkene 17 in good yield (Scheme ). Thereafter, an optimized procedure for Raghavan’s Wacker oxidation was applied to convert 17 into ketone 5 with moderate yield and excellent regioselectivity, accompanied mostly by untransformed 17 .…”

mentioning

confidence: 99%

Syntheses of the C1–C14 and C15–C25 Fragments of Amphidinolide C

2013

Org. Lett.

View full text Add to dashboard Cite

Divergent syntheses of the C1-C14 and C15-C25 fragments of amphidinolide C have been achieved. The synthesis of the C15-C25 fragment featured cobalt-catalyzed modified Mukaiyama aerobic alkenol cyclization and sulfur-directed regiocontrolled Wacker oxidation of an internal alkene. The C1-C14 fragment was established by alkenyllithium addition to an aldehyde followed by a challenging olefination of a highly inert C9 ketone.

show abstract

Exploiting Enantioselectivity of Hydrolases in Organic Solvents

Högberg

2008

Organic Synthesis With Enzymes in Non‐Aqueous Media

View full text Add to dashboard Cite

Enantiopure building blocks for the synthesis of 3-methyl-2-alkanols. Diastereoselective methylmetal addition to a chiral 2-methylaldehyde followed by lipase catalysed esterification

Cited by 8 publications

References 38 publications

Biocatalysis Applied to the Synthesis of Pheromones

Biocatalysis Applied to the Synthesis of Pheromones

Syntheses of the C1–C14 and C15–C25 Fragments of Amphidinolide C

Exploiting Enantioselectivity of Hydrolases in Organic Solvents

Contact Info

Product

Resources

About