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Tetrahedron Lett. 2013 Oct 9;54(41). doi: 10.1016/j.tetlet.2013.07.137.

Total Syntheses of Proposed (±)-Trichodermatides B and C.

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1
School of Pharmaceutical Science and Technology, Key Laboratory for Modern Drug Delivery and High-Efficiency, Tianjin University, Tianjin, 300072 P. R. China.

Abstract

Total syntheses of putative (±)-trichodermatides B and C are described. These efficient syntheses feature the oxa-[3 + 3] annulation strategy, leading to B and C along with their respective C2-epimers. However, these synthetic samples are spectroscopically very different from the natural products. DFT calculations of C13 chemical shifts are conducted and the predicted values are in good agreement with those of synthetic samples, thereby questioning in the accuracy of structural assignments of trichodermatides B and C.

KEYWORDS:

DFT calculations; Davis’ oxaziridine; Trichodermatides; biosynthesis; electrocyclic ring-opening; oxa-[3 + 3] annulation

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