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It has been a little over a year since the last synthesis-golf was posted. I have talked to orthocresol and would like to help revive the tag! A full FAQ post has been written on chemistry.meta.SE, explaining the premise of synthesis golf and the 'rules'. Please take a look at this before answering (if you haven't already).


Hyperielliptone HA is a phloroglucinol extracted by Wu et al1 in 2008. The compound is of particular interest because of its highly unique structure and demonstration of DNA oxidation inhibition.

Hyperielliptone HA

Rules:

  • Your synthesis must involve a method for the preparation of the phloroglucinol core.

  • Your synthesis must be stereoselective; however, the stereocenter attached to the phloroglucinol core can be racemic. Bonus points if you can develop a stereoselective synthesis for this moiety!

  • All reagents must be available from Sigma Aldrich.

  • If you do not have time to complete the entire synthesis but have a clever idea for a specific moiety, feel free to share your answer.


References

  1. Wu, C.; Yen, M.; Yang, S.; Lin, C. Phloroglucinols with Antioxidant Activity and Xanthonolignoids from the Heartwood of Hypericum geminiflorum. J. Nat. Prod. (2008) 71 (6), 1027-1031. DOI:10.1021/np8001145.
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  • $\begingroup$ HINT: This compound exist in two tautomeric forms. This might make conceptualizing this molecule a bit easier -- it's good to tackle a synthesis by looking at the molecule from multiple angles! $\endgroup$ – Eli Jones May 18 '20 at 9:07
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    $\begingroup$ If you have not yet thought about it; maybe you would like to submit a synthesis. $\endgroup$ – Martin - マーチン May 24 '20 at 9:19

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