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Macrocyclization by Ring-Closing Metathesis in the Total Synthesis of Natural Products: Reaction Conditions and Limitations   

25 August 2006 6,564 views 5 Comments

pinnatoxin.jpg
Pérez-Castells and Gradillas. ACIEE, 2006, Early View. DOI: 10.1002/anie.2006006410.

This review article covers the ever-popular RCM step in natural product synthesis. The range of architectures is impressive, as you might expect, as is the range of ring-sizes. However, a certain theme develops as this paper contains 24, count them, reference to Alois Fürstner’s work.

However, the scope of the article is good, detailing the conditions used in each synthesis, and those condition which failed. RCM (and metathesis in general) is a relatively new field, and we as organic chemists are still getting to grips with the power of this reaction, but this paper makes for a great reference/tool kit.

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5 Comments

  • Tot. Syn. says:

    PS. Props to Herr Doctor Ryan for mentioning this one to me…

  • JM says:

    Not your fault Total Syn as it is wrong in the review, but the structure of pinnatoxin is wrong – rather than a 4-membered cyclic bis-acetal, it is actually a 5-membered cyclic acetal.

  • J says:

    Ahaha, you’ll never win Tot. Syn guy. Even if you draw the structure as they had it in the article, you’re still doomed to get one person telling you that you drew it wrong. YOU’RE CURSED! CURSED I TELL YOU!

  • Mitch says:

    It’s his lot in life. ;)

    Mitch

  • Tot. Syn. says:

    Chaps,
    Thanks for the comments – it’s good to be informed, corrected, and kept in my place (!). Still, I’d rather get it wrong here, than in an Angewandte review…