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. 2011 Mar 7;50(11):2511-5.
doi: 10.1002/anie.201007613. Epub 2011 Feb 18.

Synthesis and biological evaluation of ABCD ring fragments of the kibdelones

David L Sloman  1 , Branko Mitasev, Stephen S Scully, John A Beutler, John A Porco Jr
Affiliations

Synthesis and biological evaluation of ABCD ring fragments of the kibdelones

David L Sloman et al. Angew Chem Int Ed Engl. .
No abstract available

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Figures

Figure 1
Figure 1
Representative Polycyclic Xanthone Natural Products
Figure 2
Figure 2
X-Ray Structure of Biaryl Dimer 18
Figure 3
Figure 3
Possible Active Intermediates for Pt(IV)-mediated Arylation
Figure 4
Figure 4
X-ray crystal structure of 19
Scheme 1
Scheme 1
Proposed cycloaddition of heterocyclic quinone 8 and styrene 9
Scheme 2
Scheme 2
Reagents and conditions: a) 2:1 pyridine: butyric-anhydride reflux; b) 2.0M MeNH2THF RT, CSA, toluene, 85 °C; c) BBr3, THF −78 °C-rt; d) Ag2O, CHCl3; e) AlCl3, pyridine, CH2Cl2 ; f) Li2CO3, MeI, DMF 45 °C; g) TBDPS-Cl, DMAP, TEA, CH2Cl2; h) MCPBA CH2Cl2, NaHCO3, MeOH 0 °C; i) vinyl tributyltin, Pd(PPh3)4, toluene 85 °C. ; THF = tetrahydrofuran, CSA = camphor sulfonic acid, DMAP = 4-dimethylaminopyridine, MCPBA = m-chloroperoxybenzoic acid.
Scheme 3
Scheme 3
Reagents and conditions: a) BCl3, THF −78 °C-RT b) PIDA, MeOH 0 °C-RT c) NCS, PPh3, DMA. PIDA = Iodobenzene diacetate, NCS = N-chloro-succinimide, DMA =dimethylformamide.
Scheme 4
Scheme 4
Reagents and conditions: a) hν (Pyrex filter), cyclohexane; b) TBAF, THF 0 °C. TBAF = tetrabutylammonium fluoride.
Scheme 5
Scheme 5
Reagents and conditions: a) acetyl chloride, DIEA CH2Cl20 °C; b) CAN, CH3CN/ pH 7 buffer 0 °C; c) HF-pyrdine, THF 0 °C d) Otera’s catalyst, 2:1 toluene:MeOH 70 °C; e) Na2S2O4 H2O:EtOAc. DIEA = disopropylethylamine, THF = tetrahydrofuran CAN = ceric ammonium nitrate.
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