Abstract
An efficient synthesis of the C4-epi-lomaiviticin B core is reported. The synthesis features a diastereoselective anionic formal furan Diels-Alder reaction and a stereoselective oxidative enolate dimerization. During the investigation, subtle yet critical stereoelectronic effects imparted by the C4-stereocenter were observed.
Highlights
The lomaiviticins comprise a family of type-II polyketide natural products with remarkable C2-symmetric structures (Figure 1)
We discovered that treatment of with LDA14 provided the DielsAlder product in 64% yield as a 10:1 mixture of separable diastereomers, favoring the expected cis-5,5 fusion product
We have reported a synthesis of the C4-epilomaiviticin A and B cores, the first time this has been achieved in our lab
Summary
The Harvard community has made this article openly available. Please share how this access benefits you. Organic Letters 15 (10) (May 17): 2390–2393. doi:10.1021/ol400832r
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