B.R.S.M. The Battlefield Earth of organic chemistry blogs

17Aug/112

(–)-N-Methylwelwitindolinone C Isothiocyanate

Update: 13/09/11. I have reworded the introduction considerably as the original version of this paragraph described work by Rawal and coworkers in this area unfairly. Having reread the papers and what I'd written I couldn't leave things as they were. The original text can be found in [5] at the end of the article.

Sorry things have been so quiet around here lately - moving out of the flat I've lived in for the past three years, having no internet and applying for conferences have made blogging tricky. I was a bit worried that someone'd beat me to this as it's such a nice bit of work, and Tot. Syn. did on Sunday, but I'd mostly finished this by then, so here's my take anyway.

Total Synthesis of (–)-N-Methylwelwitindolinone C Isothiocyanate

Garg et al., J. Am. Chem. Soc., 2011, ASAP; [PDF][SI][GROUP]

DOI: 10.1021/ja206538k

There's been a lot of interest in these unusual looking natural products in the past decade with publications from Wood, Trost, Baran, Simpkins, Martin and Rawal all appearing in the literature. Credit for the first total synthesis of a member of this family goes to Rawal and coworkers, who reported a neat route to racemic N-methylwelwitindolinone D isonitrile back in March of this year, unfortunately before I'd started this blog.[1,2] This paper by Garg describes the first synthesis of N-methylwelwitindolinone C isothiocyanate to date, using a chiral pool based approach from (S)-carvone, and also contains lots of interesting chemistry.

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11Jun/110

(+)-Liphagal

The Catalytic Enantioselective Total Synthesis of (+)-Liphagal

Stoltz et al., Angew. Chem. Int. Ed., 2011, Early View; [PDF] [SI] [GROUP HOMEPAGE]

DOI: 10.1002/anie.20110184

This tetracyclic meroterpene has had quite a bit of attention from the synthetic community since its isolation back in 2006 from a Caribbean sponge. Along with other well known natural products such as resveratrol, staurosporine, and wortmannin it's an inhibitor of phosphatidylinositol 3-kinase (PI3K), an enzyme involved in numerous diseases. The fact that those all have wikipedia pages is quite telling. It's also got some cytotoxicity towards various cancer cell lines, but I suspect the reason people keep making it is the unique and interesting 6-7-5-6 ring system.

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