A Short Stereoselective Synthesis of (+)-<i>cis</i>-Planococcyl Acetate, Sex Pheromone of the Citrus Mealybug<i>Planococcus citri</i>(Risso)

Wolk, Joel L.; Goldschmidt, Zeev; Dunkelblum, E.

doi:10.1055/s-1986-31613

Cited by 28 publications

(7 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Despite the absence of comprehensive studies on the scope of the reaction and its comparison to the original process using silver, the Cristol–Firth modification was extensively used as a method for the selective introduction of a halogen. The reaction was used almost exclusively to introduce bromine, and very few examples of the corresponding iododecarboxylation are reported. ,− Examples of the chlorination reaction were surprisingly absent, likely due to the inconvenience of using chlorine gas.…”

Section: Pioneering and Classical Methodsmentioning

confidence: 99%

Decarboxylative Halogenation of Organic Compounds

2020

View full text Add to dashboard Cite

Decarboxylative halogenation, or halodecarboxylation, represents one of the fundamental key methods for the synthesis of ubiquitous organic halides. The method is based on conversion of carboxylic acids to the corresponding organic halides via selective cleavage of a carbon–carbon bond between the skeleton of the molecule and the carboxylic group and the liberation of carbon dioxide. In this review, we discuss and analyze major approaches for the conversion of alkanoic, alkenoic, acetylenic, and (hetero)aromatic acids to the corresponding alkyl, alkenyl, alkynyl, and (hetero)aryl halides. These methods include the preparation of families of valuable organic iodides, bromides, chlorides, and fluorides. The historic and modern methods for halodecarboxylation reactions are broadly discussed, including analysis of their advantages and drawbacks. We critically address the features, reaction selectivity, substrate scopes, and limitations of the approaches. In the available cases, mechanistic details of the reactions are presented, and the generality and uniqueness of the different mechanistic pathways are highlighted. The challenges, opportunities, and future directions in the field of decarboxylative halogenation are provided.

show abstract

Section: Pioneering and Classical Methodsmentioning

confidence: 99%

Decarboxylative Halogenation of Organic Compounds

2020

View full text Add to dashboard Cite

show abstract

“…28 There have been several syntheses of the female sex pheromone of the citrus mealy bug, cis-planococcyl acetate, based on cis-pinonic or cis-pinononic acids. 29,30 The radical obtained by irradiation of the thiohydroxamic acid derivative 33 of pinonic acid was captured with bromine from BrCCl 3 to give the nor-bromide 34 (Scheme 7). 34 This was used in a modification of these syntheses.…”

Section: Chiral Cyclobutane Synthonsmentioning

confidence: 99%

Chiral Cyclic Synthetic Intermediates from Readily Available Monoterpenoids

Hanson

2015

Journal of Chemical Research

View full text Add to dashboard Cite

show abstract

“…The cyclobutane moiety is a structural feature present in several natural or designed products with interesting biological properties (Moglioni et al, 2000). Some researchers have synthesized many bioactive substances, such as sex pheromones (Wolk et al, 1986), juvenile hormones (Ribas et al, 1980) etc. Thus, using pinonic acid as a starting material, we may synthesize new cyclobutane derivatives with biological properties.…”

Section: S1 Commentmentioning

confidence: 99%