Total synthesis

Source: Wikipedia, the free encyclopedia.

Total synthesis is the complete

inorganic,[5][6]
though these are rarely encountered. Total synthesis projects often require a wide diversity of reactions and reagents, and subsequently requires broad chemical knowledge and training to be successful.

Often, the aim is to discover a new route of synthesis for a target molecule for which there already exist known routes. Sometimes, however, no route exists, and chemists wish to find a viable route for the first time. Total synthesis is particularly important for the discovery of new

chemical reagents, as well as establishing synthetic routes for medicinally important compounds.[7]

Scope and definitions

There are numerous classes of natural products for which total synthesis is applied to. These include (but are not limited to):

polypeptides and polynucleotides. The peptide hormones oxytocin and vasopressin were isolated and their total syntheses first reported in 1954.[9]
It is not uncommon for natural product targets to feature multiple structural components of several natural product classes.

Aims

Although untrue from an historical perspective (see the

Scripps, a notable pioneer of practical synthesis have endeavored to create scalable and high efficiency syntheses that would have more immediate uses outside of academia.[17][18]

History

retrosynthesis presents the disassembly of the target vitamin in a manner that makes chemical sense for its eventual forward construction. The target, Vitamin B12 (I), is envisioned being prepared by the simple addition of its tail, which had earlier been shown to be feasible. The needed precursor, cobyric acid (II), then becomes the target and constitutes the "corrin
core" of the vitamin, and its preparation was envisaged to be possible via two pieces, a "western" part composed of the A and D rings (III) and an "eastern" part composed of the B and C rings (IV). The restrosynthetic analysis then envisions the starting materials required to make these two complex parts, the yet complex molecules V–VIII.

Friedrich Wöhler discovered that an organic substance, urea, could be produced from inorganic starting materials in 1828. That was an important conceptual milestone in chemistry by being the first example of a synthesis of a substance that had been known only as a byproduct of living processes.[2] Wöhler obtained urea by treating silver cyanate with ammonium chloride, a simple, one-step synthesis:

AgNCO + NH4Cl → (NH2)2CO + AgCl

Tainionkoski, Finland
, in 1907.

The American chemist Robert Burns Woodward was a pre-eminent figure in developing total syntheses of complex organic molecules, some of his targets being cholesterol, cortisone, strychnine, lysergic acid, reserpine, chlorophyll, colchicine, vitamin B12, and prostaglandin F-2a.[2]

Vincent du Vigneaud was awarded the 1955 Nobel Prize in Chemistry for the total synthesis of the natural polypeptide oxytocin and vasopressin, which reported in 1954 with the citation "for his work on biochemically important sulphur compounds, especially for the first synthesis of a polypeptide hormone."[19]

Another gifted chemist is Elias James Corey, who won the Nobel Prize in Chemistry in 1990 for lifetime achievement in total synthesis and for the development of retrosynthetic analysis.

List of notable total syntheses


References

  1. ^ "Archived copy". Archived from the original on 2014-12-20. Retrieved 2015-08-22.{{cite web}}: CS1 maint: archived copy as title (link)
  2. ^
    PMID 10649349
    .
  3. ISBN 978-3-527-29231-8
  4. ISBN 978-3-527-30684-8
  5. PMID 23610005
    . Retrieved 15 July 2021.
  6. doi:10.1002/ange.19630751827
    .
  7. doi:10.1021/acs.chemrev.5b00034
  8. ISBN 978-0-387-85498-4
    . Retrieved 24 June 2021.
  9. doi:10.1021/ja01641a004
    .
  10. ISBN 978-94-009-0255-8
    . Retrieved 24 June 2021.
  11. doi:10.31635/ccschem.019.20190006
    .
  12. PMID 32319494
    .
  13. ^ Qualmann, Kate (15 August 2019). "Excellence in Industrial Organic Synthesis: Celebrating the Past, Looking to the Future". ACS Axial. ACS Axial. Retrieved 24 June 2021.
  14. PMID 29635919
    .
  15. PMID 30613812
    .
  16. ^ Derek, Lowe. "How Healthy is Total Synthesis". In The Pipeline (AAAS). The American Association for the Advancement of Science. Retrieved 24 June 2021.
  17. ^ "Phil Baran Research". Phil Baran Research Lab. Scripps Institute. Retrieved 24 June 2021.
  18. S2CID 224825988
    . Retrieved 24 June 2021.
  19. Nobel Media AB
    . Retrieved 17 November 2016.
  20. ^ Remembering Organic Chemistry Legend Robert Burns Woodward, "C&EN", 4/10/2017
  21. ^ Rao, R. Balaji. (2016). Logic of Organic Synthesis. LibreTexts.
  22. doi:10.1016/S0160-9327(00)01310-7

External links
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