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Author: Subject: Lugdunomycin
Tsjerk
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[*] posted on 23-8-2019 at 00:19
Lugdunomycin


Look at this beauty! A completely novel structure found not to long ago. Named after the city I live. My girlfriend was one of the people who found it ;)

"Lugdunomycin has unique structural characteristics, including a heptacyclic ring system, a spiroatom, two all-carbon stereocenters, and a benzaza-[4,3,3]propellane motif"

Article


lugdunomycin.PNG - 25kB

Attachment: MolView.mol (5kB)
This file has been downloaded 152 times

At least now I can't use it in the guess the compound game anymore :)

[Edited on 23-8-2019 by Tsjerk]
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[*] posted on 23-8-2019 at 02:32


I had to look up what a spiroatom was: the only common atom of two rings.

Is there a special significance to it having a spiroatom?




i am wg48 but not on my usual pc hence the temp handle.

Thank goodness for Fleming and the fungi.
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Tsjerk
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[*] posted on 23-8-2019 at 09:48


Just speculating, but it could be relevant as it makes the quite extreme 3D structure possible.
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Metacelsus
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[*] posted on 23-8-2019 at 14:12


Wow, that looks like a beast.

Anyone up for a total synthesis? :D




As below, so above.
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CuReUS
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[*] posted on 24-8-2019 at 11:15


Quote: Originally posted by Metacelsus  
Anyone up for a total synthesis? :D
thought you would never ask ;)

My method ( sans stereo :D )

1.thermal rearrangement of molecule A

2.diels alder with molecule B
B.png - 1kB

3.demethylation of phenol using BBr3

4.double oxidation of the benzylic positions using SeO2

5.protection of phenol using TIPS (Q)

6.conversion of the bottom ketone to gem-dibromide using PBr5 - https://www.embibe.com/study/reaction-of-aldehydes-and-keton...

7.Modified corey house reaction with molecule C
C.png - 2kB
Quote:
From the stoichiometry, it is apparent that one equivalent of the R group is wasted as an ill-characterized alkylcopper species (likely polymeric; usually converted to RH upon aqueous workup) in the most common form of the Corey–House synthesis. To avoid this for cases where R is a precious or complex fragment, a reagent (R)(RU)CuM, where RU is an untransferable dummy ligand (e.g., RU = cyano, alkynyl, 2-thienyl, etc.) can be prepared and used instead.
https://en.wikipedia.org/wiki/Corey%E2%80%93House_synthesis#...

8.demethylation of phenol using BBr3 followed by williamson ether synthesis

9.removal of TIPS(Q) using nBu4NF- ,followed by methylation

10.debenzylation using H2/Pd/C

11.glycol hydrolysis to reveal the cyclopentanone

12.double NaBH4 reduction of ketones to get the target compound

lugdonomycin.png - 23kB

[Edited on 24-8-2019 by CuReUS]
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[*] posted on 24-8-2019 at 11:26


Lugdunomycin versus Lugdunin: Why would the discoverers of a potential antibiotic choose a name that's so similar to another recently discovered antibiotic?

https://en.wikipedia.org/wiki/Lugdunin
https://www.nature.com/articles/nature18634
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Tsjerk
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[*] posted on 25-8-2019 at 06:09


The names seem similar, but are different.

about Lugdunin (or actually the species producing it):

"It was first described in 1988 after being differentiated through DNA analysis. Its name comes from Lugdunum, the Latin name for Lyon, France, where the organism was first isolated."

The name for Leiden, Netherlands is Lugdunum Batavorum, which means as much as Lyon of the Bataviers as it was named after Lyon by the Romans.

about Lugdunomycin: The Lugdun part is equal, but the ending is a reference to the species it was extracted from. Streptomycin is famous for it's name; the -mycin ending refers to it being a fungus. It is not. Decades after naming it like a fungus it was found it is actually a bacterial species which looks and behaves like a fungus.

Quote: Originally posted by CuReUS  

thought you would never ask ;)

My method ( sans stereo :D )


I love your post! I will take some time soon to have a good look at it :)

[Edited on 25-8-2019 by Tsjerk]
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CuReUS
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[*] posted on 26-8-2019 at 07:52


modified 3 step method :)

1.williamson ether synthesis with molecule A

a.png - 2kB

2. https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.2017006...

3.diels alder with molecule B

b1.png - 1kB

modified.png - 6kB

[Edited on 26-8-2019 by CuReUS]
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