34524-38-4Relevant articles and documents
De Novo Asymmetric Synthesis of Avocadyne, Avocadene, and Avocadane Stereoisomers
Cunha, Vitor L. S.,Liu, Xiaofan,Lowary, Todd L.,O'Doherty, George A.
, p. 15718 - 15725 (2019/11/19)
The de novo asymmetric synthesis of all possible stereoisomers of two polyketide natural products, avocadyne, avocadene, and the saturated variant avocadane, is described. The stereodivergent synthesis of the 12 congeners is accomplished in 4-6 steps from an achiral acylpyruvate derivative, which, in turn, is prepared in five steps from commercially available materials. The approach uses, sequentially, a Noyori asymmetric reduction, a diastereoselective chelate- or directed reduction of a β-hydroxyketone, and an ester reduction to a primary alcohol.
THE ABSOLUTE CONFIGURATION EFFECT ON THE ACTIVITY OF THE AVOCADO ROOTING PROMOTER
Becker, D.,Sahali, Y.,Raviv, M.
, p. 2065 - 2067 (2007/10/02)
16-Heptadecyn-1,2,4-triol is the most active component of the avocado rooting promotor (ARP).All four diastereoisomers of this compound have been synthesized.Their root promoting activity was determined over the physiologically active concentration range.It was found that the (2R,4R)-stereoisomer exerts a rooting activity similar to that of the extracted and purified compound from avocado tissues.The (2R,4S), and (2S,4R)-stereoisomers had lower activity and the (2S,4S)-stereoisomer had the lowest activity.It is concluded that the natural form, (2R,4R), acts in the rooting process either in its original structure or after reaction which does not alter its chiral centres.
