Catalytic asymmetric synthesis of enantiopure isoprenoid building blocks: application in the synthesis of apple leafminer pheromones.
The first catalytic asymmetric procedure capable of preparing all 4 diastereoisomers (ee > 99%, de > 98%) of a versatile saturated isoprenoid building block was developed and the value of this new method was demonstrated in its application to the concise total synthesis of two pheromones.
van Summeren
Ruben P
RP
Department of Organic and Molecular Inorganic Chemistry, Stratingh Institute, University of Groningen, Nijenborgh 4, 9747 AG, Groningen, The Netherlands.
Reijmer
Sven J W
SJ
Feringa
Ben L
BL
Minnaard
Adriaan J
AJ
D000818:Animals; D007915:Lepidoptera / Q000737:chemistry*; D015394:Molecular Structure; D010675:Pheromones / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D013729:Terpenes / Q000138:chemical synthesis* / Q000737:chemistry*
D010675:Pheromones; D013729:Terpenes