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.
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.
- 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.