期刊
TETRAHEDRON
卷 72, 期 26, 页码 3790-3794出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2016.02.040
关键词
MIDA boronates; Iterative cross-coupling; Polyene natural products; Endiandric acids; Synthesis
资金
- National Science Foundation [CHE-1058361]
- Harvey Mudd College
- Henry Dreyfus Teacher-Scholar Award
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1058361] Funding Source: National Science Foundation
Both fused and bridged tetracyclic scaffolds characteristic of endiandric acid-type natural products have been prepared in just seven steps each (longest linear sequence) from Burke's commercial cis-2-bromovinylboronic acid MIDA ester. Three iterative Suzuki-Miyaura couplings using MIDA boronates, including the first such example of a Z-Z coupling, trigger an 8 pi/6 pi-electrocyclization cascade. The mixture of endo and exo bicycles thus formed are elaborated into tetracycles via Horner-Wadsworth-Emmons and Diels-Alder reactions. In the process, the endo and exo diastereomers interconvert to ultimately deliver the desired products. (C) 2016 Elsevier Ltd. All rights reserved.
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