Studies toward brevisulcenal F via convergent strategies for marine ladder polyether synthesis
Shortly after the initial isolation of marine ladder polyether natural products, biomimetic epoxide-opening cascade reactions were proposed as an efficient strategy for the synthesis of these compounds. However, difficulties in assembling the cascade precursors have limited the realization of these...
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Published in | Tetrahedron Vol. 74; no. 11; pp. 1111 - 1122 |
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Main Authors | , |
Format | Journal Article |
Language | English |
Published |
OXFORD
Elsevier Ltd
15.03.2018
Elsevier |
Subjects | |
Online Access | Get full text |
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Summary: | Shortly after the initial isolation of marine ladder polyether natural products, biomimetic epoxide-opening cascade reactions were proposed as an efficient strategy for the synthesis of these compounds. However, difficulties in assembling the cascade precursors have limited the realization of these cascades. In this report, we describe strategies that provide convergent access to cascade precursors via regioselective allylation and efficient fragment coupling. We then investigate epoxide-opening cascades promoted by strong bases for the formation of fused tetrahydropyrans. These strategies are evaluated in the context of the synthesis of rings CDEFG of brevisulcenal F.
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Bibliography: | NIH RePORTER ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
ISSN: | 0040-4020 1464-5416 |
DOI: | 10.1016/j.tet.2018.01.039 |