Insect Pheromones etc. (at the Univ of Tokyo)

Synthetic Studies of Insect Pheromones
Aggregation pheromones of weevils
The relative and absoluted configuration of the male-produce aggregtation pheromones of the African plam weevil and the Asian palm weevil was determined by racemic and chiral synthesis of the proposed structures.
phoenicols

4. "Synthesis of the Stereoisomers of 3-Methyl-4-octanol to Determine the Absolute Configuration of the Naturally Occuring (4S,5S) Isomer Isolated as the Male-produced Pheromone Compound of Rhynchophorus vulneratus and Metamasius hemipterus"
  K. Mori, H. Kiyota and D. Rochat, Liebigs Annalen der Chemie, 1993, 865-870 (1993).
3. "Synthesis of the Enantiomers of syn-4-Methyl-5-nonanol to Determine the Absolute Configuraion of the Naturally Occuring (3S,4S)-Isomer Isolated as the Male-produced Aggregation Pheromone of the African Plam Weevil, Rhynchophorus phoenicis"
  K. Mori, H. Kiyota, C. Malosse and D. Rochat, Liebigs Annalen der Chemie, 1993, 1201-1204 (1993).


endo-Brevicomin
(+)-endo-Brevicomin, the pheromone of the bark beetles such as western pine beetle、southern pine beetle and mountain pine beetle, was synthesized using lipase-catalyzed asymmetric acetylation as the key step.
brevicomin

2. "A New Synthesis of (3S, 4R)-8-Nonene-3,4-diol, the Key Intermediate for the Synthesis of (+)-endo-Brevicomin"
  K. Mori and H. Kiyota, Liebigs Annalen der Chemie, 1992, 989-992 (1992).

A sex pheromone of a wasp
A sex pheromone component for the wasp, Macrocentrus grandii, was synthesized by starting from methyl (R)-citronellate and employing bromolactonization as the key reaction.
wasp

6. "Synthesis of (2S,4R,5S)-2,4,6-Trimethyl-5-heptanolide, a Sex Pheromone Component for Macrocentrus grandii"
  H. Kiyota and K. Mori, Biosci. Biotech. Biochem., 58(6), 1120-1122 (1994).

A sex pheromone of maritime pine scale
A major component of the female-produced sex pheromone of the maritime pine scale (Matsucoccus feytaudi) was synthesized using enzyme-catalyzed asymmetric hydrolysis as the key step.
maritime

8. "A New Synthesis of (3S,7R,8E,10E)-3,7,9-Trimethyl-8,10-dodecadien-6-one, the Major Component of the Sex Pheromone of the Maritime Pine Scale"
  K. Mori, T. Furuuchi and H. Kiyota, Liebigs Annalen der Chemie, 1994, 971-974 (1994).

      
Dehydration of allylic alcohol
A new method to prepare dienes by dehydration of allylic alcohols was developed.

dienes

7. "Facile Preparation of Conjugated Dienes from Allylic Alcohols"
  T. Kitahara, T. Matsuoka, H. Kiyota et al., Synthesis, 1994(7), 692-694 (1994).


Reduction reaction using hydrogenomonas

Pseudomonas hydrogenothermophilaTH-1

Synthesis of cerebrosides