Chemoenzymatic synthesis of (E)-3,7-dimethyl-2-octene-1,8-diol isolated from the hairpencils of male Danaus chrysippus (African Monarch).
The synthesis of (E)-3,7-dimethyl-2-octene-1,8-diol (1), which was isolated from the hairpencils of male Danaus chrysippus (African Monarch), was investigated. The key step of the sequence involves asymmetric desymmetrization of the 1,3-propanediol 7 with lipase, in which high enantioselectivity was observed. Total synthesis afforded (S)-1 in 12 steps and 26% overall yield from readily available geraniol.
Takabe
Kunihiko
K
Department of Molecular Science, Faculty of Engineering, Shizuoka University, 3-5-1 Johoku, 432-8561, Hamamatsu, Japan. tcktaka@ipc.shizuoka.ac.jp
Mase
Nobuyuki
N
Hashimoto
Hiroya
H
Tsuchiya
Atsushi
A
Ohbayashi
Takashi
T
Yoda
Hidemi
H
D000080462:Acyclic Monoterpenes; D000421:Alcaligenes / Q000201:enzymology; D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D000475:Alkenes / Q000138:chemical synthesis*; D000818:Animals; D016956:Burkholderia cepacia / Q000201:enzymology; D002080:Butterflies / Q000737:chemistry*; D002175:Candida / Q000201:enzymology; D002384:Catalysis; D008049:Lipase / Q000737:chemistry* / Q000378:metabolism; D008297:Male; D011409:Propylene Glycols / Q000737:chemistry; D011551:Pseudomonas fluorescens / Q000201:enzymology; D013237:Stereoisomerism; D013729:Terpenes / Q000737:chemistry
D000080462:Acyclic Monoterpenes; D000438:Alcohols; D000475:Alkenes; D011409:Propylene Glycols; D013729:Terpenes; C041787:1,3-propanediol; D008049:Lipase; C007836:geraniol