6001. 1-Methoxy-3-(trimethylsilyloxy)-1,3-butadiene
Nomenclature
CAS number: 54125-02-9 (E-form);
59414-23-2
(unspecified stereo)
[[(2E)-3-Methoxy-1-methylene-2-propenyl]oxy]trimethylsilane; Danishefsky's diene. C8H16O2Si; mol wt 172.30.
C 55.77%, H 9.36%, O 18.57%, Si 16.30%.
Description and references
A silyl enol ether used in Diels-Alder reactions; highly reactive and nucleophilic diene. Prepn and 1H-NMR: S. Danishefsky, T. Kitahana, J. Am. Chem. Soc. 96, 7807 (1974); S. Danishefsky et al., Org. Synth. 61, 147 (1983). In synthesis of vernolepin, q.v.: eidem, J. Am. Chem. Soc. 99, 6066 (1977); of pentalenolactone: eidem, ibid. 100, 6536 (1978). Regiospecific addition to juglone, q.v.: R. K. Boeckman et al., ibid. 7098. Review: S. Danishefsky, Acc. Chem. Res. 14, 400 (1981).
