Day, A.J.George, J.H.2020-09-152020-09-152020Journal of natural products, 2020; 83(7):2305-23090163-38641520-6025http://hdl.handle.net/2440/127882Reinvestigation of the coumarin meroterpenoids of Philotheca myoporoides using pressurized hot water extraction (PHWE) procedures led to the isolation of prenylbruceol A, a proposed biosynthetic precursor of seven previously reported bruceol derivatives, prenylbruceols B-H. Protobruceol-I, ostruthin, dipetalactone, and a new dihydrocoumarin natural product were isolated alongside prenylbruceol A. A biomimetic singlet oxygen ene reaction of prenylbruceol A allowed the semisynthesis of prenylbruceols B, C, and D.en© 2020 American Chemical Society and American Society of PharmacognosyRutaceaeBiological ProductsSpectrum AnalysisBiomimeticsMolecular StructureOxidation-ReductionJournal article100002426810.1021/acs.jnatprod.0c003480005555170000302-s2.0-85088389869538384George, J.H. [0000-0002-7330-2160]