Iterative synthesis of (oligo)deoxypropionates via zinc-catalyzed enantiospecific sp3-sp3 cross-coupling.
This group's recently reported mild zinc-catalyzed enantiospecific sp3-sp3 cross-coupling of lactic acid tert-butylester triflate with Grignard reagents was now applied to an iterative approach in the synthesis of a series of all four possible diastereomers of the shown trideoxypropionate. Oligodeoxypropionate structures are a common motif in a large number of biologically relevant natural products of polyketide origin thus making our approach a versatile tool in their synthesis.
Brand
Gabriel J
GJ
Institut für Organische Chemie und Biochemie, Freiburg Institute for Advanced Studies (FRIAS), Albert-Ludwigs-Universität Freiburg, Albertstrasse 21, 79104 Freiburg, Germany.
Studte
Christopher
C
Breit
Bernhard
B
D002384:Catalysis; D011108:Polymers / Q000138:chemical synthesis* / Q000737:chemistry*; D011422:Propionates / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity; D015032:Zinc / Q000737:chemistry*
D011108:Polymers; D011422:Propionates; D015032:Zinc