Chen X, Fong JZ, Xu J, Mou C, Lu Y, Yang S, Song BA, and Chi YR
Journal of the American Chemical Society [J Am Chem Soc] 2016 Jun 15; Vol. 138 (23), pp. 7212-5. Date of Electronic Publication: 2016 Jun 02.
Abstract
Carbene-catalyzed reaction of carboxylic esters has the potential to offer effective synthetic solutions that cannot be readily achieved by using the more conventional aldehyde-type substrates. Here we report the first carbene-catalyzed dynamic kinetic resolution of α,α-disubstituted carboxylic esters with up to 99:1 er and 99% yield. The present study clearly illustrates the unique power of carbene-catalyzed reactions of readily available and easy to handle carboxylic esters.
Ding F, William R, Leow ML, Chai H, Fong JZ, and Liu XW
Organic letters [Org Lett] 2014 Jan 03; Vol. 16 (1), pp. 26-9. Date of Electronic Publication: 2013 Dec 02.
Subjects
Alkaloids chemistry, Molecular Conformation, Pyridones chemistry, Alkaloids chemical synthesis, and Pyridones chemical synthesis
Abstract
A diverted total synthesis (DTS) approach to the total synthesis of pyridone alkaloids N-deoxymilitarinone A (8) and torrubiellone B (10) has been developed. The common intermediate 14 was first assembled by a dual directed orthometalation process using a methoxymethyl group as directed metalation group. Other crucial steps include the assembly of polyenes under aldol condensation for DTS using general and concise strategy and diastereoselective synthesis of the syn-dimethyl array by an Evans aldol reaction.
