Thiocyanate synthesis by C-S coupling or subsitution
We report the first total synthesis of (−)--methylwelwitindolinone C isothiocyanate. Our route features a number of key transformations, including an indolyne cyclization to assemble the [4.3.1]-bicyclic scaffold, as well as a late-stage intramolecular nitrene insertion to functionalize the C11 bridgehead carbon en route to the natural product.
Categories: C-S Bond Formation > Synthesis of thiocyanates
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.
Scientific research has shown that Wasabi produces a suite of biomedically active molecules called isothiocyanates (ITCs) which are powerful nutraceuticals. These compounds, particularly the long chain methyl isothiocyanate, 6MITC, are most abundant in authentic Wasabi. It is these ITCs that are responsible for the flavour and heat of real Wasabi as well as the unique health benefits including: anti-allergies, anti-oxidant, anti-cancer, antibiotic (ulcers), anti-inflammatory, immune boost and anti-coagulant. In addition, other natural compounds from Wasabi are effective in bone calcification and collagen synthesis.