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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Bibliographic Details
Published inTetrahedron Vol. 74; no. 11; pp. 1111 - 1122
Main Authors Katcher, Matthew H., Jamison, Timothy F.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 15.03.2018
Elsevier
Subjects
Cascade reactions
Chemistry
Chemistry, Organic
Epoxide openings
Natural products
Oxygen heterocycles
Physical Sciences
Polyethers
Science & Technology
Epoxide openings
Polyethers
Oxygen heterocycles
Natural products
Cascade reactions
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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. [Display omitted]
Bibliography:NIH RePORTER
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ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2018.01.039