TY - JOUR
T1 - Exploitation of chemical predisposition in synthesis
T2 - An approach to the manzamenones
AU - Al-Busafi, Saleh
AU - Doncaster, Jeremy R.
AU - Drew, Michael G.B.
AU - Regan, Andrew C.
AU - Whitehead, Roger C.
PY - 2002
Y1 - 2002
N2 - Full details of the syntheses of manzamenones A, C and F are reported, using an approach modelled on a plausible biogenetic theory. The key step of the approach is a "one-pot" conversion of the antileukemic cyclopentenone, untenone A, to manzamenone A which occurs in reasonable yield and which proceedsvia a reaction sequence of dehydration, Diels-Alder dimerisation and retro-Dieckmann reaction. The synthetic approach has also been applied to the preparation of a number of shorter alkyl chain analogues of the natural products. Using a combination of NMR and X-ray crystallographic data for the shorter alkyl chain analogues of manzamenone A, it is suggested that the relative stereostructures of the majority of the manzamenones should be revised such that the acyl group at the C2 position lies on α-face and that at the C5 position resides on the β-face.
AB - Full details of the syntheses of manzamenones A, C and F are reported, using an approach modelled on a plausible biogenetic theory. The key step of the approach is a "one-pot" conversion of the antileukemic cyclopentenone, untenone A, to manzamenone A which occurs in reasonable yield and which proceedsvia a reaction sequence of dehydration, Diels-Alder dimerisation and retro-Dieckmann reaction. The synthetic approach has also been applied to the preparation of a number of shorter alkyl chain analogues of the natural products. Using a combination of NMR and X-ray crystallographic data for the shorter alkyl chain analogues of manzamenone A, it is suggested that the relative stereostructures of the majority of the manzamenones should be revised such that the acyl group at the C2 position lies on α-face and that at the C5 position resides on the β-face.
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U2 - 10.1039/b110829h
DO - 10.1039/b110829h
M3 - Article
AN - SCOPUS:0036008089
SN - 1472-7781
VL - 4
SP - 476
EP - 484
JO - Journal of the Chemical Society. Perkin Transactions 1
JF - Journal of the Chemical Society. Perkin Transactions 1
ER -