Cordigol Progress

Alan Spivey and co-workers at Imperial College have recently published in Organic Letters on a SnCl4-mediated Prins cyclization to form the ring system of cordigol.

OL paper

Three Component Approach for Cyclic Nitrones

Milan Potacek and co-workers at Masaryk University have recently published in Tetrahedron on a three component coupling approach for synthesizing 5-membered-cyclic nitrones.

Tetrahedron paper

Tangutorine Synthesis

Here’s a nice alkaloid total synthesis by Yasumasa Hamada and co-workers at Chiba University.

OL paper

A Failed Inverse Electron Demand Diels-Alder

Craig Lindsley and co-workers at Vanderbilt have recently published in Organic Letters on their attempt at an inverse electron demand Diels-Alder reaction to access marineosin.  That reaction would have been cool if they got it to work.  It’s interesting that they published a failed biosynthetic proposal route – but fortunately they are not giving up on the synthesis and now they are going to approach the synthesis with a different route.

OL paper

[5+2] then Nazarov

Paul Wender and co-workers have recently published in JACS on a rhodium catalyzed [5+2] cycloaddition followed by Nazarov protocol.

JACS paper

Synthesis of Chloptosin

Zhu-Jun Yao and co-workers at the Shanghai Institute of Organic Chemistry have recently published in Organic Letters on the total synthesis of a C2-symmetric cyclopeptide, chloptosin, which induces apoptosis in human pancreatic adenocarcinoma cell lines AsPC-1 with an EC₅₀ of 2.5 micrograms per mL.  This molecule is an important lead because many human carcinoma cells are resistant to apoptosis.

OL paper

Vinylogous Aldol

Masahiro Terada and co-workers at Tohoku University have used an organocatalytic approach to perform vinylogous Aldol reactions using a C2-symmetric guanidine base.

ACIEE paper

Idesolide Synthesis

Yoshiharu Iwabuchi and co-workers at Tohoku University have recently published in Organic Letters on the synthesis of idesolide from a dimerization of a cyclohexenone starting material.  The dimerization step involved the use of AZADO (2-azaadamantane-N-oxyl).

OL paper

AZADO paper

Cyanolide A

William Gerwick and co-workers at UC San Diego have recently published in the Journal of Natural Products on the isolation of cyanolide A, a glycosidic macrolide, from the bacteria, Lyngbya bouillonii, from Papua, New Guinea. This dimeric macrolide was found to kill molluscs – specifically Biomphalaria glabrata with an LC50 of 1.2 micromolar. This biological activity is important because these snails carry parasites that cause schistosomiasis.

JNP paper

Multi-Component Fe-Catalysis

Umasish Jana and co-workers at Jadavpur University in India have recently published in JOC on a multicomponent approach towards substituted pyrroles using an iron (III) catalyst.

JOC paper