Enantioselective Synthesis of the Sex Pheromone of Lichen Moth, Miltochrista calamine, and Its Diastereomer

Synlett ◽  
2021 ◽  
Author(s):  
Jiangchun Zhong ◽  
Gucheng Yuan ◽  
Jiawei Liu ◽  
Shihang Yu ◽  
Xueyang Wang ◽  
...  
Keyword(s):  
Sex Pheromone ◽  
Enantioselective Synthesis ◽  
Synthetic Approach ◽  
Chiral Auxiliaries ◽  
Synthetic Sex Pheromone ◽  
Key Steps

AbstractThe synthesis of a Miltochrista calamine sex pheromone and its diastereomer has been developed. The key steps of the synthetic approach involved Evans’ chiral auxiliaries and the addition of alkyne to aldehyde, which were firstly applied to prepare this sex pheromone and its diastereomer. The synthetic sex pheromone could be used to trap insects and study physiological and ecological questions of the lichen moth.

A Concise Enantioselective Synthesis of (S)-Preclamol via Asymmetric Catalytic Negishi Cross-Coupling Reaction

Synlett ◽  
2019 ◽  
Vol 30 (07) ◽  
pp. 860-862 ◽  
Author(s):  
Yun Zhou ◽  
Chunxiao Liu ◽  
Lifeng Wang ◽  
Leng Han ◽  
Shicong Hou ◽  
...  
Keyword(s):  
Total Yield ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Enantioselective Synthesis ◽  
Synthetic Approach ◽  
Chiral Drugs ◽  
Asymmetric Catalytic ◽  
Cross Coupling Reaction ◽  
Tertiary Carbon ◽  
Key Steps

A novel, concise, and efficient enantioselective synthesis of (S)-preclamol (87% ee, 51% total yield) has been developed. The key steps of this synthetic approach included cobalt-catalyzed asymmetric catalytic cross-coupling of α-bromo ester with arylzinc and the reduction of chiral ester to diol with a tertiary carbon atom. Moreover, it was demonstrated that our enantioselective Negishi cross-coupling was a powerful tool to construct stereogenic benzylmethyl center in chiral drugs on a gram scale.

scholarly journals Asymmetric total synthesis of a putative sex pheromone component from the parasitoid wasp Trichogramma turkestanica

2014 ◽  
Vol 10 ◽  
pp. 761-766 ◽  
Author(s):  
Danny Geerdink ◽  
Jeffrey Buter ◽  
Teris A van Beek ◽  
Adriaan J Minnaard
Keyword(s):  
Sex Pheromone ◽  
Total Synthesis ◽  
Parasitoid Wasp ◽  
Conjugate Addition ◽  
Enantioselective Synthesis ◽  
Pheromone Component ◽  
Asymmetric Total Synthesis ◽  
Catalytic Asymmetric ◽  
Key Steps

Virgin females of the parasitoid wasp Trichogramma turkestanica produce minute amounts of a sex pheromone, the identity of which has not been fully established. The enantioselective synthesis of a putative component of this pheromone, (6S,8S,10S)-4,6,8,10-tetramethyltrideca-2E,4E-dien-1-ol (2), is reported as a contribution to this identification. Catalytic asymmetric conjugate addition of methylmagnesium bromide and stereoselective Horner–Wadsworth–Emmons olefinations are used as the key steps, and 2 was obtained in 16 steps with an overall yield of 4.4%.

scholarly journals Design, Synthesis, and Biological Evaluation of the Sex Pheromone of the Asian Corn Borer, Ostrinia furnacalis (Guenée)

2018 ◽  
Vol 2018 ◽  
pp. 1-7 ◽  
Author(s):  
Zhengchang Lu ◽  
Wei Liu ◽  
Hongyu Pan ◽  
Dawei Zhang
Keyword(s):  
Sex Pheromone ◽  
Cost Effective ◽  
Biological Evaluation ◽  
Synthetic Approach ◽  
Isomer Ratio ◽  
Mass Trapping ◽  
Ostrinia Furnacalis ◽  
Corn Borer ◽  
Tetradecenyl Acetate ◽  
Synthetic Sex Pheromone

A convenient total synthesis of (Z)-12-tetradecenyl acetate (1a) and (E)-12-tetradecenyl acetate (1b), which are the sex pheromones of Ostrinia furnacalis (Guenée), has been achieved. The target mixture molecules, of a cis-to-trans-isomer ratio of 27 to 73, were synthesized in 40% overall yield and through [13C + 1C] synthetic strategy in five steps from commercially available and cheap industrial brassylic acid as key starting material. The electroantennogram (EAG) responses of synthetic sex pheromone to ACB male moths were conducted. The results showed that the target mixture molecules were found to have a good activity and displayed significantly stronger EAG responses ranging from 10 to 1000 μg, and the optimized stimulating dosage of the activity of synthetic sex pheromone to ACB males is 10 μg. Compared with the existing routes, this synthetic approach is operationally simple, good-yielding, and cost-effective, which could serve as a basis for developing the techniques of sex pheromone mass trapping or mating disruption and providing an environmentally benign method to control ACB pests.

scholarly journals Practical Synthesis and Field Application of the Synthetic Sex Pheromone of Rice Stem Borer, Chilo suppressalis (Lepidoptera: Pyralidae)

2020 ◽  
Vol 2020 ◽  
pp. 1-9 ◽  
Author(s):  
Bin Liu ◽  
Kun-Jie Syu ◽  
Yuan-Xin Zhang ◽  
Sachin Gupta ◽  
Yu-Jhe Shen ◽  
...  
Keyword(s):  
Sex Pheromone ◽  
Field Tests ◽  
Stem Borer ◽  
Field Application ◽  
Chilo Suppressalis ◽  
Synthetic Strategy ◽  
Rice Stem Borer ◽  
Synthetic Sex Pheromone ◽  
Key Steps ◽  
Long Chain

Rice stem borer, Chilo suppressalis, is a common and major serious pest of rice, maize, and wheat crops across Asia, Europe, and Oceania countries. Its sex pheromone consists of three analogously compounds, i.e., (Z)-hexadec-11-enal (1), (Z)-octadec-13-enal (2), and (Z)-hexadec-9-enal (3), as long-chain aliphatic internal cis-alkenyl aldehydes. In order to perform an economic and widespread pest control management of rice stem borer, a versatile and efficient synthetic strategy is required. A versatile and efficient synthesis using a common synthetic route for cis-alkenals with high overall yields is described. Commercially available inexpensive aliphatic diols were chosen as starting materials. Two key steps were employed to synthesize the long-chain aliphatic internal cis-alkenes in excellent yields, including the alkylation of terminal alkynes without the utilization of a highly polar aprotic cosolvent and the versatile cis-selective semihydrogenation for the reduction of internal alkynes with excellent stereoselectivity. The results of field tests showed that the synthetic sex pheromone blend was highly effective for the capture of rice stem borer.

scholarly journals Studies on the Enantioselective Synthesis of E-Ethylidene-bearing Spiro[indolizidine-1,3′-oxindole] Alkaloids

Molecules ◽  
2021 ◽  
Vol 26 (2) ◽  
pp. 428
Author(s):  
Nihan Yayik ◽  
Maria Pérez ◽  
Elies Molins ◽  
Joan Bosch ◽  
Mercedes Amat
Keyword(s):  
Ring System ◽  
Enantioselective Synthesis ◽  
Synthetic Route ◽  
Hydroxymethyl Group ◽  
Hydride Reduction ◽  
Lactam Carbonyl ◽  
Key Steps ◽  
Oxindole Alkaloids

A synthetic route for the enantioselective construction of the tetracyclic spiro[indolizidine-1,3′-oxindole] framework present in a large number of oxindole alkaloids, with a cis H-3/H-15 stereochemistry, a functionalized two-carbon substituent at C-15, and an E-ethylidene substituent at C-20, is reported. The key steps of the synthesis are the generation of the tetracyclic spirooxindole ring system by stereoselective spirocyclization from a tryptophanol-derived oxazolopiperidone lactam, the removal of the hydroxymethyl group, and the stereoselective introduction of the E-ethylidene substituent by acetylation at the α-position of the lactam carbonyl, followed by hydride reduction and elimination. Following this route, the 21-oxo derivative of the enantiomer of the alkaloid 7(S)-geissoschizol oxindole has been prepared.

The influence of behaviour modifying chemicals on mating success of the red bollworm Diparopsis castanea Hmps. (Lepidoptera, Noctuidae) in Malawi

1976 ◽  
Vol 66 (2) ◽  
pp. 279-300 ◽  
Author(s):  
R. J. Marks
Keyword(s):  
Sex Pheromone ◽  
Sexual Attraction ◽  
Practical Method ◽  
Pheromone Trap ◽  
Cotton Field ◽  
Field Cage ◽  
Synthetic Sex Pheromone ◽  
Trap Catches ◽  
First Time ◽  
Lepidoptera Noctuidae

AbstractThe synthetic sex pheromone (dicastalure) of the red bollworm of cotton, Diparopsis castanea Hmps., in Central and Southern Africa, and an inhibitor of male sexual attraction (trans-9-dodecenyl acetate,=IIA), were used in an enclosed 0·2 ha cotton field-cage to reduce successful female matings. Over one month dicastalure at 21·0 and 42·3 g/ha produced average reductions in mating of 47·9% and 72·5% respectively and 37·9 g IIA/ha produced an overall reduction in mating of 71·5%, or 79·5% in released moth populations, over the same period. The proportion of virgin females present in disruption situations was significantly greater than in untreated populations and was density-independent for moth populations of up to 2 200/ha. The proportion of fertile eggs in disruption situations was correspondingly reduced to 30·2% from an average of 67·9% in control cycles. Reduction in sex pheromone trap catches is an unsatisfactory indicator of the extent to which males are prevented from inseminating females and considerably over-estimates the true degree of disruption. This is the first time that a naturally occurring inhibitor has been used successfully to disrupt mating in a field population of insects and it indicates the potential of the method for the control of high density pest populations in cotton. However, use of polyethylene dispensing mechanisms similar to those used in the field-cage disruption experiments would be unsuitable as a practical method of dispensing behaviour modifying chemicals and it is suggested that, for suitably controlled release of such chemicals, currently available microencapsulation technology offers the best prospects.

Isolation, identification, synthesis, and bioefficacy of female Diacrisia obliqua (Arctiidae) sex pheromone blend. An Indian agricultural pest

2001 ◽  
Vol 73 (7) ◽  
pp. 1157-1162 ◽  
Author(s):  
J. S. Yadav ◽  
M. Y. Valli ◽  
A. R. Prasad
Keyword(s):  
Sex Pheromone ◽  
Female Sex Pheromone ◽  
Wittig Olefination ◽  
Pheromone Components ◽  
Diacrisia Obliqua ◽  
Seed Crops ◽  
Key Steps ◽  
Sex Pheromone Blend ◽  
Pheromone Blend ◽  
Oil Seed Crops

Diacrisia obliqua is a polyphagous pest especially on oil seed crops. Adult female sex pheromone blend consists of five pheromone components, which include (3Z,6Z)-cis-9,10-epoxyl,3,6-henicosatriene and (3Z,6Z)-cis-9,10-epoxy3,6-henicosadiene. Synthesis of these enantiomers was achieved through alkylative epoxide rearrangement and stereoselective Wittig olefination reactions as key steps. Bioefficacy experiments both at laboratory and minifield were very positive.

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