The [4 + 3]-cycloaddition/quasi-Favorskii process. Synthesis of the carbocyclic core of tricycloclavulone.
[reaction: see text] The [4 + 3]-cycloadduct derived from the reaction of 2,5-dibromocyclopentanone with cyclopentadiene was converted via a quasi-Favorskii rearrangement and ring-opening, ring-closing metathesis sequence to the carbocyclic core of the prostanoid tricycloclavulone.
Harmata
Michael
M
Department of Chemistry, University of Missouri-Columbia, Columbia, Missouri 65211, USA. harmatam@missouri.edu
Wacharasindhu
Sumrit
S
D000818:Animals; D037421:Anthozoa / Q000737:chemistry; D003500:Cyclization; D015394:Molecular Structure; D011453:Prostaglandins / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
D011453:Prostaglandins; C463699:tricycloclavulone