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[29 Mar 2006 | 4 Comments | 3,851 views]

Sun et al. J. Nat. Prod., 2006, ASAP. DOI: 10.1021/np060047j
Interesting new isolation from Schisandra lancifolia. The stereochemistry around the cyclopentane should be tricky enough to put in, and there’s plenty of opportunity for racemisation alpha to those carbonyls…!

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[29 Mar 2006 | 5 Comments | 6,165 views]

Crimmins and DeBaillie. JACS, 2006, ASAP. DOI: 10.1021/ja057686l
All in the name, this one. Obviously a bisamide, so even the undergrads would get the major disconnections in this one! They put the spiroketal in very nicely though, alkylating and hydrogenating to give the desired product in 83% over two steps.

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[28 Mar 2006 | 2 Comments | 7,444 views]

Smith, Mesaros & Meyer. JACS, 2006, ASAP. DOI: 10.1021/ja060369+
Another synthesis by Amos Smith’s Group, this time of the macrolide Kendomycin, which they build up from four main fragments, resulting in a nicely convergent synthesis. As you might expect, the isolated double-bond is produced via a RCM step, completing the macrocycle. However, the olefin geometry was unfortunately inverse to the target, so an isomerisation was required. They tried to isomerise with iodine (always worth a go), but to no avail, as with the Vedejs and Oshima isomerisations, so they used technique …

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[28 Mar 2006 | Comments Off | 6,895 views]

Smith, Davulcu & Kürti. Org. Lett., 2006, ASAP. DOI: 10.1021/ol0602912, 10.1021/ol060290+
Two Org. Lett.s by Amos Smith this week on the Nodulisporic acids (D&F). Before you think this is all about building those quaternary carbon centres, they started with them built in!

No, these papers are about construction of the the indole system, building ring B to fuse with A and then constructing C, all in 7 steps. Very neat and powerful. So, in other words, good heterocycle lessons for those pharma interviews.

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[27 Mar 2006 | 2 Comments | 9,218 views]

Overman, Garg & Hiebert. ACIE, 2006, EarlyView. DOI: 10.1002/anie.200600417
Rather strange looking beast; two fused macrocycles in a pentacyclic system. The final cyclisation goes via a Stille coupling, using the trans- vinyl stannane and a cis- vinyl iodide. However, more interesting to me was the condensation approach for creation of the eight-member ring in 86%. Nice.

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[26 Mar 2006 | One Comment | 12,473 views]

Hatakeyama, Fukumoto, Takahashi & J. Ishihara. ACIE, 2006, 45, 1. DOI: 10.1002/anie.200600210
Nice new Angewandte, using a tandem RCM approach for assembly of two of the rings. The Lewis-acid mediated cyclisation of the epoxide was rather sweet, too.