- A Short and Efficient Approach for the Total Synthesis of (S)-Zearalenone and (R)-De-O-methyllasiodiplodin by Using Stille and RCM Protocols
-
A concise, flexible, and linear approach has been devised for the total synthesis of the resorcinylic acid lactones (S)-zearalenone (2) and (R)-de-O-methyllasiodiplodin (4) by using a Stille cross-coupling strategy. The other key steps of the synthesis include a ring-closing metathesis (RCM), a chemoselective reduction of an α,β-unsaturated ketone, and a transesterification reaction.
- Kumar Dey, Sujit,Ataur Rahman, Mohammad,Alkhazim Alghamdi, Ahmad,Reddy, Basi V. Subba,Yadav, Jhillu S.
-
p. 1684 - 1692
(2016/04/05)
-
- Catalytic asymmetric total synthesis of (S)-(-)-zearalenone, a novel lipoxygenase inhibitor
-
A catalytic asymmetric synthesis of (S)-(-)-zearalenone is reported using asymmetric allylic alkylation for the introduction of the stereocenter. (S)-(-)-Zearalenone turned out to be a novel lipoxygenase inhibitor.
- Baggelaar, Marc P.,Huang, Yange,Feringa, Ben L.,Dekker, Frank J.,Minnaard, Adriaan J.
-
p. 5271 - 5274
(2013/09/02)
-
- A concise total synthesis of (S)-zearalenone and zeranol
-
A convergent total synthesis of the naturally occurring, 14-membered macrolides (S)-zearalenone and zeranol has been achieved through application of the Diels-Alder reaction, Jacobsen kinetic resolution, Mitsunobu coupling, ring-closing metathesis, and hy
- Yadav,Murthy, P. Vishnu
-
p. 2117 - 2124
(2011/08/05)
-
- A novel biomimetic synthesis of (S)-(-)-zearalenone: Via macrocyclization and transannular aromatization
-
On heating, a hydroxy-keto-dioxinone underwent retro-Diels-Alder fragmentation and the resultant α,γ-diketo-ketene was efficiently trapped intramolecularly by a secondary alcohol to provide a macrocyclic triketo-lactone. Following ketal hydrolysis, transannular aromatization gave the resorcylate natural product, (S)-(-)-zearalenone.
- Miyatake-Ondozabal, Hideki,Barrett, Anthony G.M.
-
experimental part
p. 6331 - 6334
(2010/10/19)
-
- Solid-phase synthesis of macrocyclic systems by a cyclorelease strategy: Application of the stille coupling to a synthesis of (S)-zearalenone
-
No heteroatom required! In many solid-phase syntheses, after the release from the polymer support a heteroatom (e.g. O, S, N) remains in the substrate as a residue of a linking protecting group. With polymer-bound tin reagents cleavage and cyclization of
- Nicolaou,Winssinger, Nicolas,Pastor, Joaquin,Murphy, Fiona
-
p. 2534 - 2537
(2007/10/03)
-
- Total Synthesis of the Mycotoxin (-)-Zearalenone based on Macrocyclisation using a Cinnamyl Radical Intermediate
-
A concise synthesis of optically active (-)-zearalenone, which uses a novel 14-endo-trig macrocyclisation from a cinnamyl radical intermediate onto an α,β-enone electrophore as a key feature, is described.
- Hitchcock, Stephen A.,Pattenden, Gerald
-
p. 1323 - 1328
(2007/10/02)
-
- Thermostable Enzymes in Organic Synthesis, Part 6. Total synthesis of (S)-(-)-Zearalenone using a TBADH-Generated Trifunctional Chiron
-
Chiral alcohols produced by Thermoanaerobium brockii alcohol dehydrogenase (TBADH)-catalysed asymmetric reduction of polyfunctional ketones are useful building blocks for natural products synthesis.In particular, the ability of TBADH to discriminate between two ketones having equal chemical reactivity is demonstrated by enzymatic reduction of dec-9-ene-2,6-dione to produce optically pure (S)-2-hydroxydec-9-en-6-one.The total synthesis of (S)-(-)-zearalenone with optical purity that exceeds 99.5percent has been achieved by using the latter compound as a starting material.
- Keinan, Ehud,Sinha, Subhash C.,Sinha-Bagchi, Anjana
-
p. 3333 - 3340
(2007/10/02)
-
- Synthesis of β-Resorcylic Macrolides via Organopalladium Chemistry. Application to the Total Synthesis of (S)-Zearalenone
-
The β-resorcyclic macrolides are a class of naturally occurring 12- and 14-membered macrolides.Zearalenone (1), a 14-membered macrolide of this type, displays useful biological activity, which has led to great synthetic interest.In this paper the intramolecular coupling reaction of an organostannane with an electrophile is used to construct β-resorcylic macrolides.The intramolecular coupling of an aryl iodide with a vinylstannane provided the highest yield of lactones.This methodology was then used to prepare (S)-zearalenone (1).
- Kalivretenos, A.,Stille, J. K.,Hegedus, L. S.
-
p. 2883 - 2894
(2007/10/02)
-
- Steroid ethers
-
Novel steroid ethers are disclosed, which are represented by the formula: STR1 wherein Z is selected from the group consisting of >C=O >CHOH, and STR2 X is selected from the group consisting of --H and --OH, and R is selected from the group consisting of
- -
-
-