Raghavan, Sadagopan; Patel, Javed Sardar published the artcile< A Stereoselective Synthesis of the Carbon Backbone of Phoslactomycin B>, Category: thiazole, the main research area is stereoselective synthesis carbon backbone phoslactomycin B; propargylic sulfide rearrangement unsaturated ketone phoslactomycin B synthesis; aldol stereoselective phoslactomycin B synthesis; asym transfer hydrogenation phoslactomycin B synthesis; diyne partial reduction phoslactomycin B synthesis.
A convergent synthesis of the entire carbon framework of phoslactomycin B (I) is disclosed. An initial route aimed to create the C-8 tetrasubstituted stereocenter through regioselective intermol. coupling between an internal alkyne and an allyl silyl ether, adopting Trost’s protocol, followed by [2,3] sigmatropic rearrangement. But this was not successful. In a second approach, a propargylic sulfide was rearranged to give an unsaturated ketone. This was then treated with lithio acetonitrile to create the C-8 stereocenter selectively. The C-4 and C-5 stereocenters were introduced by a non-Evans syn-aldol reaction using Crimmins’s protocol. The C-9 and C-11 carbinol centers were created by asym. transfer hydrogenation. The (Z,Z)-diene moiety was introduced by partial reduction of a diyne following Hansen’s modification of the Boland reduction reaction.
European Journal of Organic Chemistry published new progress about Aldol addition, stereoselective. 171877-39-7 belongs to class thiazole, and the molecular formula is C10H11NS2, Category: thiazole.
Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica