Samir BouzBouz

Synthetic efforts toward the macrolactone core of Leucascandrolide A.

A chemoselective synthesis of 1, the macrocyclic core of leucascandrolide A, has been achieved by utilizing highly enantioselective allylmetalations, an enantioselective Noyori reduction of a propargylic ketone, and olefin metatheses as the key steps.

Ring opening of cyclopropylketones induced by photochemical electron transfer

Abstract Depending on the substitution pattern of cyclopropylketones, the photochemically induced electron transfer of tertiary amines to cyclopropylketones leads either to the formation of 3-substituted cycloalkanones or to ring expanded products.

Tandem reaction by using compatible catalysts: Cross-metathesis reaction and hydrogenation

Abstract A one-pot tandem cross-metathesis/hydrogenation procedure was achieved at room temperature, under one atmosphere of hydrogen, in the presence of ruthenium catalyst II and PtO 2 showing the compatibility of the two catalysts.

A SHORT ACCESS TO (+)-PTILOCAULIN

Abstract A short access to (+)-ptilocaulin involving a photoreductive cyclopropane ring opening of an optically active bicyclo[4.1.0]heptanone derivative is described.

Enantioselective allyltitanations: synthesis of the proposed structures for passifloricin A

Abstract The stereoselective total synthesis of the proposed structures P1 and P2 for passifloricin A was achieved in 12 steps from n -hexadecanal by using enantioselective allyltitanations and a ring closing metathesis reaction as the key steps. Both P1 and P2 are different from passifloricin A.

Acryloyl Chloride: An Excellent Substrate for Cross-Metathesis. A One-Pot Sequence for the Synthesis of Substituted α,β-Unsaturated Carbonyl Derivatives

A diverse set of functionalized alpha,beta-unsaturated carbonyl compounds were synthesized in good yield by utilizing a very simple one-pot process involving a cross-metathesis between acryloyl chloride and a terminal olefin followed by the addition of a nucleophile.

Enantioselective allyltitanation. Application to the synthesis of lactone units related to compactin and mevinolin

Abstract The enantioselective convergent synthesis of two different models of the lactone units of compactin and mevinolin was achieved using two consecutive enantioselective allyltitanations of aldehydes.

Formal Synthesis of Dictyostatin and Synthesis of Two Dictyostatin Analogues

A formal convergent synthesis of dictyostatin from (R)-Roche ester is described. Synthetic highlights include a Ni-catalyzed Nozaki-Hiyama-Kishi coupling between an aldehyde and a Z vinyl iodide to assemble the two main fragments, a diastereoselective Myers alkylation, a stereoselective Evans aldolization, two asymmetric Duthaler crotyltitanations, and a stereoselective Pd-catalyzed Marshall allenylindium addition to install the stereogenic centers of dictyostatin. The synthesis of (9R)-epi-dictyostatin and a new ring-contracted dictyostatin isomer were also achieved.

Cross‐Metathesis Reaction: Direct Synthesis of Functionalized Allylsilanes

Cross-metathesis between α,β-unsaturated carbonyl compounds and allylsilanes with Hoveydas catalyst leads to functionalized allylsilanes in moderate to good yields and with excellent E/Z stereoselectivity in favor of the E-isomer.

Enantioselective synthesis of propargylic alcohols by addition of enantiopure cyclopentadienyldialkoxyallyltitanium complexes to acetylenic aldehydes

Abstract The enantioselective synthesis of propargylic alcohols was achieved by enantioselective allyltitanation of acetylenic aldehydes.