Catalytic asymmetric aldehyde prenylation and application in the total synthesis of (-)-rosiridol and (-)-bifurcadiol.

Catalytic asymmetric aldehyde prenylation and application in the total synthesis of (-)-rosiridol and (-)-bifurcadiol.
Chem Commun (Camb). 2020 Jul 30;:
Authors: Zhang YL, Zhao ZN, Li WL, Li JJ, Kalita SJ, Schneider U, Huang YY
Abstract
Chiral phosphoric acid-catalyzed asymmetric aldehyde prenylation has been established using an α,α-dimethyl allyl boronic ester. The transformation provides expedient access to a wide array of aryl, heteroaryl, aryl-substituted alkenyl and primary and secondary aliphatic homoprenyl alcohols with excellent asymmetric induction. The utility of this asymmetric catalysis strategy has been demonstrated through a short and efficient total synthesis of the two natural products (-)-rosiridol and (-)-bifurcadiol.
PMID: 32728678 [PubMed - as supplied by publisher]

Source: Chemical Communications - July 29, 2020 Category: Chemistry Authors: Zhang YL, Zhao ZN, Li WL, Li JJ, Kalita SJ, Schneider U, Huang YY Tags: Chem Commun (Camb) Source Type: research