Home » Archive

Articles tagged with: [2+2]

Still In The RBF »

[26 Sep 2009 | 53 Comments | 20,043 views]
Biyouyanagin A

Xie, Du, Li, Li. ACIEE, 2009, ASAP. DOI: 10.1002/anie.200902908.
A second showing for this complex little target, Zhixiang Xie’s route uses the same end-game as that developed by Nicolaou two years ago.  However, getting to that point is a very different matter, using some quite powerful chemistry.  The RHS of the molecule is a distinct natural product – hyperolactone C, with the LHS also natural – zingiberene.  The latter was produced as in Nicolaou’s paper, but hyperolactone – the more challenging portion – was produced in a rather different …

Still In The RBF »

[21 Jul 2009 | 32 Comments | 21,323 views]
Tricholomalides A & B

Danishefsky, Wang, Min. JACS, 2009, ASAP. DOI: 10.1021/ja9049433.
I’m still wading through the bumper-Tetrahedron issue flagged-up in the comments, but halfway through reading Amos Smiths spongistatin epic I noticed a new Danishefsky paper in JACS.  So whilst I man-handle Amos’ tour-d’force into bite-sized-chunks, here’s a smart slice of typical Danishefsky.
Initial work on the target was published in a rather nice Tet. Lett. last year, and that’s where the synthetic action starts.  A well known Robison Annulation created a 6,5-fused enone in a racemic fashion, which Danishefsky cyclopropanated …

Still In The RBF »

[30 Mar 2008 | 16 Comments | 8,561 views]

Tadano, Takao, Hayakawa, Yamada, Yamaguchi, Morita and Kawasaki, ACIEE, 2008, EarlyView. DOI: 10.1002/anie.200800253.
Mentioned in the comments, this tidy little synthesis features one hell of a tightly functionalised ring system, with seven contiguous stereocentres and a trans- trisubstituted olefin in a ten-membered ring. The biological activity seems impressive too: cytotoxicity and immunosuppressive activity, but the potency isn’t mentioned in this paper. This is actually the first synthesis of pestalotiopsin A, even though it’s recieved plenty of attention from the Procter and Paquette groups. Retro time:

Circumventing …