D.V. Yashunsky

Left and right-half taxoid building blocks from (S)-(+)-Hajos-Parrish ketone

Abstract An efficient 11-step synthesis of the optically homogeneous bridged ring system 4 , and a 5-step synthesis of the cyclohexane derivative 5a from Hajos-Parrish ketone is presented.

Studies towards the total synthesis of taxoids. A straightforward procedure for the taxoid BC substructure

Abstract The aldol condensation of the ketone 6 and the aldehyde 7 followed by an annelation-fragmentation afforded the bicyclo[6.4.0]dodecane derivative 3 with the appropriate functionalities for further elaboration.

Studies towards the total synthesis of taxoids synthesis of an A-ring building unit

An efficient 11-step synthesis of the optically homogeneous bridged ring system 13, by a Sml2 mediated reductive pinacol coupling is presented.

A chemoenzymatic approach to the taxoid BC-substructure

Abstract The synthesis of a homochiral taxoid BC-unit containing the required functionalities on the B-ring periphery and a conveniently functionalized C-ring moiety by combination of enzymatic hydrolysis and the aldol-annelation-fragmentation sequence is described.

Regio- and stereochemical variations in Diels-Alder reactions

Abstract The AB+D ABCD approach for the synthesis of the tetracyclic intermediates 3–6 is reinvestigated. Water, high-pressure, LiCl and scandium triflate-mediated Diels-Alder reactions of 1 and 2 are reported.

Studies towards the total synthesis of taxoids: An efficient formal total synthesis of an A-seco taxane framework

Compounds 6 and 19 embodying the whole carbon framework and suitable functionalities of the taxane skeleton have been assembled starting from readily available chemicals.

Formal total synthesis of an A-seco mevinic acid

Abstract Combined use of chemical and enzymatic methods for a short access to the fully functionalized B-ring, the 2′, 1′, 8a, 4a-tetrasubstituted cyclohexene unit, of A-seco mevinic acids is presented.

Lead tetraacetate mediated “one-pot” multistage transformations on selected unsaturated 1,2-diols: The Wieland-Miescher series

Abstract Starting with the unsaturated diol 6 , a rapid entry into fused bicyclic derivative 8 and hence to the bridged ring system 11 (both one-pot processes) is achieved.

Studies towards the total synthesis of taxoids. Lead tetraacetate oxidations of selected unsaturated bicyclic diols

Syntheses of potential C-1/C-15 and C-2/C-10 subunits of taxoid skeleton 1 using lead tetraacetate cleavage of the Wieland-Miescher ketone derived diol 6 and the Hajos-Parrish ketone derived diol 14 are described.

An efficient route to the formal total synthesis of A-seco mevinic acid analogues

Abstract A short, stereocontrolled access to the fully functionalized B-ring together with a chemobiological approach to the 1,2,3,4-tetrasubstituted cyclohexene unit of A-seco mevinic acids is presented.