Total synthesis of the sesquiterpene (+/-)-illudin C via an intramolecular nitrile oxide cycloaddition.

  title={Total synthesis of the sesquiterpene (+/-)-illudin C via an intramolecular nitrile oxide cycloaddition.},
  author={Ronald Alan Aungst and C. M. Chan and Raymond L. Funk},
  journal={Organic letters},
  volume={3 16},
[reaction: see text] A convergent total synthesis of illudin C is described. The tricyclic ring system of the natural product was quickly assembled from cyclopropane and cyclopentene precursors via a novel oxime dianion coupling reaction and a subsequent intramolecular nitrile oxide-olefin cycloaddition. 
23 Citations
Sterically Controlled Diels–Alder Cycloadditions: Rapid Entry into the Illudin Scaffold
Rapid entry into the tricyclic ring system of the illudin family of natural products was achieved using a Diels–Alder cycloaddition of allylidenecyclopropane 7 and various cyclic and acyclic
Rapid construction of the ABD tricyclic skeleton in meliacarpinin B from carvone enabled by an INOC strategy
A highly diastereoselective synthesis of the ABD skeleton of meliacarpinin B is presented. The construction of the key trans-decalin unit features an intramolecular nitrile oxide-alkene cycloaddtion
Reaction of Nitrile Oxides with Masked o‐Benzoquinones; Synthesis of Highly Functionalized Isoxazolines
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This chapter comprises the utilization of oximes for the synthesis of various biologically active molecules such as ptilocaulin, amphotericin, macrolides, etc.
Convergent assembly of structurally diverse quinazolines.
A convergent and versatile Vilsmeier-Haack-based carbo-annulation strategy that exhibits an unusually elevated bond-forming efficiency has been developed and enables the rapid assembly of structurally diverse quinazoline chemotypes.


Vilsmeier Formylation of O-Silylated Enolates of Carboxylic Esters. A New Method for the Synthesis of α-Formylcarboxylic Esters
Synthese en particulier de formyl-2 butyrates et methyl-2propionates d'ethyle et de formyl-1 cyclopentane- et cyclohexane-carboxylate de methyle
A Convenient Synthesis of 4,4-Dimethylcyclopentenone
Abstract 4,4-Dimethylcyclopentenone 1 has attracted a considerable amount of attention as a useful substrate for photochemical studies1, and more recently for the synthesis of
Reduction of .DELTA.2-isoxazolines. 3. Raney nickel catalyzed formation of .beta.-hydroxy ketones
On determine les conditions optimales de transformation d'isoxazolines-2 en β-hydroxycetones en utilisant un catalyseur Ni de Raney, l'acide borique, un melange 5/1 methanol/eau et l'hydrogene gazeux
(Hydroxymethyl)acylfulvene: an illudin derivative with superior antitumor properties.
Reaction of the fungal sesquiterpene illudin S with excess paraformaldehyde in dilute H2SO4 gives (hydroxymethyl)acylfulvene, which was more toxic than a precursor, acylful vene, but less toxic than the parent compound illud in S to HL 60 cells.
A new method for the generation of nitrile oxides and its application to the synthesis of 2-isoxazolines
(1992). A CONVENIENT METHOD FOR THE GENERATION OF NITRILE OXIDE AND ITS APPLICATION TO THE SYNTHESIS OF 2-ISOXAZOLINES. Organic Preparations and Procedures International: Vol. 24, No. 1, pp. 91-93.
A New Synthesis of (±)-Agarospirol and (±)-Hinesol
(±)-Agarospirol (8) and (±)-hinesol (9) were simultancously synthesized via a useful synthon in the synthesis of spirovetivane-type sesquiterpenes, i. e., (2S*, 5S*, 10R*)-2-hydroxy-6,
Michael-type addition of illudin S, a toxic substance from Lampteromyces japonicus, with cysteine and cysteine-containing peptides in vitro.
The structures of these adducts indicated that the alpha,beta-unsaturated carbonyl group in illudin S behaves as a Michael acceptor for the mercapto group in cysteine.
Structure of lampterol (illudin S).