Paul A. Grieco

Aqueous intermolecular Diels-Alder chemistry: reactions of diene carboxylates with dienophiles in water at ambient temperature

On prepare divers adduits monocycliques et bicycliques de Diels Alder par reaction de lhexadiene-3,5 oate, et de lheptadiene-4,6 oate de sodium avec divers dienophiles (benzoquinone, acroleine...) a temperature ambiante

Facile retro Diels–Alder reaction of a pentamethyltricyclo[5.2.1.02,6]decenone derivative: synthesis of (+)-15(S)-prostaglandin A2

The incorporation of methyl groups into the C(1), C(7), C(8), C(9), and C(10) positions of tricyclo[5.2.1.02,6]decenone (1) dramatically accelerates the retro Diels–Alder reaction of (3) under Lewis acid catalysis thus permitting access to synthetic natural prostaglandin A2; the X-ray crystal structure of the ammonium salt of (7) is reported.

Total synthesis of (±)-sesbanimide A and B

The total synthesis of sesbanimide A (1) and B (2) is reported which features (a) the reaction of cyclopentadiene with glyoxylic acid leading to the useful bicyclic lactone building block 3 and (b) the use of 2.5 mol dm–3 lithium perchlorate in diethyl ether to promote the conjugate addition of 1-methoxy-1-(tert-butyldimethylsiloxy)ethene to unsaturated lactone 11.

Diastereoselection in an aqueous Diels–Alder reaction: a formal total synthesis of the Inhoffen–Lythgoe diol

A formal synthesis of the Inhoffen–Lythgoe diol (1) featuring a novel intermolecular Diels–Alder strategy wherein an intact C(20) stereocentre as part of a diene unit is used to elaborate directly the stereocentres at C(13) and C(17) of the hydrindan ring system of (1), is reported.

Iminium ions as initiators and allylsilanes as terminators in polyolefin cyclizations: total synthesis of (±)-yohimbone via a vinylogous aminomethano desilylation process

A syntheses of (±)-yohimbone has been realized via a concerted iminium ion-induced polyolefin cyclization terminated by an allylsilane.

Synthetic studies on quassimarin: construction of the pentacyclic carbon skeleton

The synthesis of the pentacyclic ABCDE ring system (3), which constitutes the farthest advance toward the elaboration of quassimarin and related quassinoids, has been realized employing a metal–ammonia reduction of a dienone cf. (11)→(12).

Synthetic studies on quassinoids: construction of the BCE ring system of quassimarin and related natural products

The synthesis of the tricyclic BCE ring system (3) of quassimarin possessing seven contiguous stereocentres has been realized via a novel epoxymethano bridging reaction.