Author
Daniel Knueppel
Other affiliations: Dow AgroSciences, University of California, Santa Cruz
Bio: Daniel Knueppel is an academic researcher from University of Texas at Austin. The author has contributed to research in topics: Total synthesis & Enantioselective synthesis. The author has an hindex of 6, co-authored 9 publications receiving 204 citations. Previous affiliations of Daniel Knueppel include Dow AgroSciences & University of California, Santa Cruz.
Papers
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TL;DR: The spirooxindole ring system of citrinadin A has been synthesized with excellent control over the absolute stereochemistry at the spirocenter using a novel diastereoselective DMDO-mediated oxidative rearrangement employing an 8-phenylmenthol chiral auxiliary on the indole nitrogen.
66 citations
TL;DR: Fast and furious: Cribrostatin 6, an antimicrobial and antineoplastic agent, was the target of a total synthesis where the longest linear sequence was only four steps.
Abstract: The total synthesis of antimicrobial and antineoplastic cribrostatin 6 was accomplished in only four steps in the longest linear sequence and five total steps from commercially available starting materials. The key step employed a tandem 4-π electrocyclic ring opening, radical cyclization, and homolytic aromatic substitution sequence to afford the tricylic core of the natural product, which was converted to cribrostatin 6 via a subsequent, one-pot oxidation.
58 citations
TL;DR: In this article, the indium-mediated Barbier-type enantioselective allylation of both aromatic and aliphatic aldehydes using commercially available (1 S, 2 R )-(+)-2-amino-1,2-diphenylethanol as a chiral auxiliary was reported.
38 citations
TL;DR: A total synthesis of the aglycone of IB-00208 was accomplished in 22 steps using a newly developed approach towards polycyclic 1,4-dioxygenated xanthones from benzocyclobutenones using ring-closing metathesis (RCM).
20 citations
TL;DR: A new approach to polycyclic 1,4-dioxygenated xanthones from benzocyclobutenones has been developed and applied to the first total synthesis of the aglycone of IB-00208, a mixture of hydroquinone–quinone tautomers.
18 citations
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538 citations
TL;DR: The Morita-Baylis-Hillman (MBH) carbonates (II, (IV), and (VII) serve as C3 synthons in asymmetric [3 + 2] annulation reactions to give a series of 3-spirocyclopentene-2-oxindoles with two contiguous quaternary centers such as (III, (V), or (VIII) as present in various alkaloids as discussed by the authors.
Abstract: The Morita—Baylis—Hillman (MBH) carbonates (II), (IV), and (VII) serve as C3 synthons in asymmetric [3 + 2] annulation reactions to give a series of 3-spirocyclopentene-2-oxindoles with two contiguous quaternary centers such as (III), (V), or (VIII) as present in various alkaloids.
353 citations
269 citations
TL;DR: This review focuses on the various strategies for the enantioselective synthesis of spirocyclic oxindoles relying on reports over the past decade and from earlier work.
Abstract: Spirooxindoles are important synthetic targets possessing extended biological activity and drug discovery applications. This review focuses on the various strategies for the enantioselective synthesis of spirocyclic oxindoles relying on reports over the past decade and from earlier work. The spirooxindoles in this review are separated into three structural classes, and then further categorized into the method type from which the spirocycle is generated.
254 citations
201 citations