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. 2001 Sep 3;42(36):6231-6233.
doi: 10.1016/S0040-4039(01)01227-8. Epub 2001 Aug 9.

Asymmetric hetero Diels-Alder route to quaternary carbon centers: synthesis of (-)-malyngolide

Arun K Ghosh  1 , Michio Shirai  1
Affiliations

Asymmetric hetero Diels-Alder route to quaternary carbon centers: synthesis of (-)-malyngolide

Arun K Ghosh et al. Tetrahedron Lett. .

Abstract

Conformationally constrained chiral bis(oxazoline)-metal complex catalyzed asymmetric hetero Diels-Alder reactions of Danishefsky's diene and a variety of α-keto esters constructed quaternary carbon centers enantioselectively. The reaction was utilized in the synthesis of (-)-malyngolide.

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Figures

Figure 1.
Figure 1.
Scheme 1.
Scheme 1.
(a) NaBH4, CeCl3·7H2O, EtOH/H2O, 0°C; (b) K-10, CH3OH, 0–23°C (56%); (c) LiAlH4, Et2O, 0°C; (d) H2, Pd-C, CH3OH, 23°C; (e) BnBr, NaH, DMF, 0°C (56%, three steps); (f) Jones’ reagent, acetone, 23°C (60%); (g) LHMDS, HMPA, CH3I, THF, −78°C (96%).
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