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Beilstein J. Org. Chem. 2009, 5, No. 71, doi:10.3762/bjoc.5.71
Graphical Abstract
Figure 1: Structures of isoplagiochins C (1) and D (2) (with aryl fragments a–d and possible conformational b...
Figure 2: Possible stereoisomers of 1 as conformers C1–C4 relative to the configurationally stable biaryl axi...
Scheme 1: Stereochemical correlation for 1 and 2. (*: configurationally stable, (*): configurationally semi-s...
Figure 3: Temperature dependent 1H NMR and assignment of methoxy signals in the tetramethyl ether 3.
Scheme 2: Strategy of synthesis for the macrocycles 5–7.
Scheme 3: Preparation of the terminal alkyne 13 as a–b part (TBATB = tetrabutylammonium tribromide).
Scheme 4: Sonogashira-type coupling to the tolane 16.
Scheme 5: Synthesis of the d building blocks 21 and 26. aThe original procedure in diluted ammonia [31] was repla...
Scheme 6: Synthesis of the tolane precursors 27 and 28 for cyclization.
Scheme 7: Synthesis of the modified macrocycles 5–7 from the dialdehyde precursors 28–30.
Scheme 8: Synthesis of the known macrocycle 3 via McMurry reaction.