Kingianin synthesis

Michael Sherburn and co-workers from Australian National University have reported in ACIE on the synthesis of kingianins A, D, and F from a poly-yne precursor.  Ledwith-Weitz salt was used to promote a Diels-Alder dimerization.

 

ACIE paper

Thiophenes from Simmons-Smith

Kanchugarakoppal Rangappa and co-workers at the University of Mysore in India have reported in Tetrahedron Letters on the synthesis of thiophenes using a Simmons-Smith reagent.

TL paper

Tormesol via Wittig

Dongjoo Lee and co-workers at Dankook University have reported in Tetrahedron on the synthesis of tormesol.  The seven membered ring was acquired from a Horner-Wadsworth-Emmons reaction.

Tetrahedron paper

Regioselective epoxide opening

Pilar López-Ram-de-Víu and co-workers have reported in Organic and Biomolecular Chemistry on an epoxide opening reaction using a Grignard reagent – and the regioselectivity is switched when they use it in the presence of copper bromide.

OBC paper

Olefin aminohydroxylation

Istvan Marko and co-workers at Université catholique de Louvain in Belgium have reported in Tetrahedron on a nice synthesis of Telaprevir using an oxaziridine and a lithium amide to functionalize an alkene.

Tetrahedron paper

Gelsemoxonine synthesis

Tohru Fukuyama and co-workers have reported in JACS on a synthesis of gelsemoxonine featuring a divinylcyclopropane–cycloheptadiene rearrangement.

JACS paper

Polychlorinated natural product

Erick Carreira and co-workers have reported in ACIEE on their synthesis of this lipid that contains eleven chlorines.

ACIEE paper

Koser’s Reagent for Tetrahydrofurans

Athannasios Giannis and co-workers at the Universitata Leipzig have used HTIB (Koser’s reagent:  [hydroxy(tosyloxy)iodo]benzene) to form tetrahydrofurans.

 

JOC paper

Isomerization with Lawesson’s Reagent

Lawesson’s reagent normally converts carbonyls to thiocarbonyls.  Emanuele Miserazzi and co-workers at GlaxoSmithKline in Italy have published in Tetrahedron Letters on a transposition of the oxidized atom in N-benzylpiperazinones when using Lawesson’s reagent.

 

TL paper

Exocyclic Methylenes

Tomasz Janecki and co-workers have published in Synlett on a nice way to make subsituted 3-methylidene-chroman-2-ones (ie:  exocyclic methylenes) via 1,4-Grignard addition folowed by Wittig.

Synlett paper