2198-92-7Relevant academic research and scientific papers
Stereochemical correction and total structure of roridin J
Matsumoto, Manami,Ito, Atsushi,Tonouchi, Akio,Okazaki, Masaaki,Hashimoto, Masaru
, p. 5430 - 5435 (2017)
The (2′Z)-configuration of roridin J (1) was revised to the (2′E) form by conducting NOE experiments. Although the configurations with respect to the stereogenic carbons on the macrocyclic ring of 1 had remained unknown, a combination of NMR analysis and molecular modeling calculations revealed the (2′E,5′R,6′S,7′E,9′Z,13′S) form. In addition, the modeling calculations successfully reproduced the 1H and 13C NMR chemical shifts as well as the ECD spectrum. An X-ray crystallographic analysis verified all the relative configurations.
Total synthesis of (-)-verrucarol
Ishihara, Jun,Nonaka, Rie,Terasawa, Yuki,Shiraki, Ryota,Yabu, Kazuo,Kataoka, Hiromi,Ochiai, Yuichi,Tadano, Kin-Ichi
, p. 2679 - 2688 (2007/10/03)
We have achieved the total synthesis of (-)-verrucarol, a trichothecene sesquiterpenoid obtained as a hydrolysis product of the naturally occurring verrucarin A. Our total synthesis began with the previously reported enantiometrically pure bicyclic α-methylated γ-lactone, which was prepared from D-glucose. The key steps for the total synthesis were (1) aldol-like carbon-carbon bond formation applied to the starting lactone using a four- carbon aldehyde as an electrophile for introduction of the quaternary stereogenic carbon sharing the B and C-rings of the trichothecene skeleton, (2) Dieckmann cyclization of the derived ε-ester lactone for construction of the C-ring equivalent, (3) Barton's decarboxylative oxygenation for conversion of a carboxylic acid functionality in the Dieckmann cyclization product into a hydroxyl group, (4) skeletal enlargement strategy for the crucial trichothecene skeleton construction, and (5) the final stereoselective formation of the exo-epoxy ring at the methylene carbon in the bridge constituting the B and C-rings.
Total synthesis of (-)-verrucarol, a component of naturally occurring verrucarin A
Ishihara, Jun,Nonaka, Rie,Terasawa, Yuki,Shiraki, Ryota,Yabu, Kazuo,Kataoka, Hiromi,Ochiai, Yuichi,Tadano, Kin-Ichi
, p. 8311 - 8314 (2007/10/03)
Total synthesis of (-)-verrucarol (1) was achieved starting from D- glucose-derived bicyclic lactone 4 through 1) a stereoselective asymmetric quaternization of the α-carbon of the lactone, 2) Diechmann cyclization for access to the C-ring equivalent, 3) a skeletal rearrangement for the trichothecene ring system, and 4) the final stereoselective epoxidation of an exo-methylene group.
RORIDIN L-2, A NEW TRICHOTHECENE
Bloem, Russell J.,Smitka, Tim A.,Bunge, Richard H.,French, James C.,Mazzola, Eugene P.
, p. 249 - 252 (2007/10/02)
The structure (2) of roridin L-2 is shown to be a C29-trichothecene that lacks the macrocyclic lactone system usually present in the roridins.
Isolation and Characterization of the Trichoverroids and New Roridins and Verrucarins
Jarvis, Bruce B.,Stahly, G. Patrick,Pavanasasivam, Gowsala,Midiwo, Jacob O.,DeSilva, Tuley,Holmlund, Chester E.
, p. 1117 - 1124 (2007/10/02)
Myrothecium verrucaria grown on a large scale (760 L) has yielded a variety of new trichothecenes including the nonmacrocyclic trichoverroids 13-19, which contain a pendant C4 cis,trans-dienic ester side chain normally common only to the macrocyclic roridins and verrucarins.Several novel macrocyclic trichothecenes (roridins J and K acetate) and verrucarins L and L acetate also were isolated and characterized.
The ready conversion of anguidine into verrucarol and trichodermol
Tulshian, Deen Bandhu,Fraser-Reid, Bert
, p. 4549 - 4552 (2007/10/02)
Anguidine, 1, is readily converted into verrucarol diacetate, 2d, in 85 percent yield by application of the Barton-McCombie deoxygenation procedure. To enable conversion into trichodermol, 3a, the primary hydroxyl group of verrucarol, 2a, is selectively acetylated or is selectively acetylated or preferably silylated, thereby paving the way for its deoxygenation in three simple, high-yield reactions.
