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

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Summary

Subtle Stereoelectronic Effects

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

DielsAlder reaction would be controlled by the single
This process presumably occurs via a stepwise Michael
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