NOVEL POLYPRENYL COMPOUNDS, METHOD OF PRODUCING THE SAME AND THEIR USE IN DOLICHOL PRODUCTION

摘要

There are provided polyprenyl compounds of the formula (I) wherein represent a trans-isoprene unit and a cis-isoprene unit, respectively, n is an integer of 11-19, Z1 and Z2 combinedly represent =O, =CH-COOH,=CH-COOR1, =CH-CN, =C(CN)COOR2, =CH-CO-NH2, =CH-CO-N(R3) (R4), =CH-CO-NHR5, =CH-CH2-N(R3) (R4), =CH-CH2-NHR5 or =CH-CHO or Z1 is a hydrogen atom and Z2 is -CH2COOH, -CH2COOR6, -CH(CN)COOR2, -CH2CN, -CH2-CO-NH2, -CH=CH-N(R3) (R4) or -CH2-CH=N-R5, R1, R2 and R6 each being a lower alkyl group, R3 and R4 each independently being a lower-alkyl, cycloalkyl, aryl or aralkyl group or R3 and R4 combinedly representing an alkylene group containing 2-5 carbon atoms, and R5 being a lower-alkyl, cycloalkyl, aryl or aralkyl group. These polyprenyl compounds can be synthesized starting with a polyprenol obtainable from leaves of a plant such as Ginkgo biloba or Cedrus deodara by extraction and as necessary followed by hydrolysis, or a reactive derivative thereof. The polyprenyl compounds are useful as intermediates for the synthesis of dolichol without the use of an expensive C5 chain extender.