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Beilstein J. Org. Chem. 2018, 14, 2229–2235, doi:10.3762/bjoc.14.197
Graphical Abstract
Figure 1: Masked and unmasked 1,4-dialdehyde natural products 1–6.
Scheme 1: Products of the reaction of onchidal (6) with 1-pentylamine. Reagents and conditions: 1-pentylamine...
Scheme 2: Proposed mechanism for formation of onchidal diaminated adducts.
Figure 2: Target onchidal model compounds 11–18.
Scheme 3: Synthesis of n-pentyl dialdehydes 11 and 12 and enol acetate 13. Reagents and conditions: a) n-hexa...
Scheme 4: Synthesis of cyclohexylmethyl dialdehydes 15 and 16 and enol acetate 17. Reagents and conditions: a...
Figure 3: Pyrrole product 29 and salt 30 obtained from the reaction of dialdehyde 11 with n-pentylamine.
Scheme 5: Reaction of dialdehyde 11 with excess 1-pentylamine to form 29. Reagents and conditions: (a) 1-pent...
Figure 4: Pyrrole product 31 and salt 32 obtained from reaction of dialdehyde 15 with n-pentylamine.
Figure 5: Lysine adducts arising from the reaction of onchidal (6) with lysozyme.
Figure 6: SDS-PAGE separation of lysozyme after modification with 11 (left), 13 (middle), 15 (right).
Beilstein J. Org. Chem. 2015, 11, 1991–1996, doi:10.3762/bjoc.11.215
Figure 1: Members of the panicein family of aromatic sesquiterpenoids.
Figure 2: Proposed biogenesis of panicein A2 (5).
Figure 3: Retrosynthetic analysis of panicein A2 (5).
Scheme 1: Synthesis of ketone 13.
Scheme 2: Synthesis of propargyl ether 8 through formation of trifluoroacetate intermediate 17.
Scheme 3: Synthesis of propargyl ether 8 through carbonate 18.
Scheme 4: Synthesis of panicein A2 (5).