87746-55-2Relevant academic research and scientific papers
Model Studies towards Functionalized Bisbenzannulated [5,6]-Spiroketals
Wilsdorf, Michael,Lentz, Dieter,Reissig, Hans-Ulrich
, p. 1555 - 1561 (2016/04/05)
Following up on our previous model studies on the synthesis of simple bisbenzannulated [5,6]-spiroketals we here report the preparation of new examples of this entity with a variation in their substitution pattern. The regioselective introduction of functional groups in the C-3 or C-3′ positions (rubromycin numbering) may either take place prior to the spiroketalization by α-functionalizations of the ketone moiety of the precursor or in a subsequent step by the nucleophilic substitution of the benzylic hydroxy group of the previously described C-3-hydroxylated spiroketal. By applying these methods we could synthesize new methyl-substituted, hydroxylated, halogenated and amino-substituted bisbenzannulated [5,6]-spiroketals in good overall yields. C-1 or C-3? By applying suitable methods new functionalized [5,6]-spiroketals were regioselectively generated as model compounds for rubromycin-type natural products.
A Diels-Alder strategy towards a benzonaphthopyranoquinone
Tapia, Ricardo A.,Alegría, Luz,Valderrama, Jaime A.,Cortés, Manuel,Pautet, Félix,Fillion, Houda
, p. 887 - 889 (2007/10/03)
Reaction of a suitably protected aryllithium derivative with citral, and subsequent deprotection and cyclization was used to obtain dibenzopyran 5, a precursor of the tricyclic quinone 6. Diels-Alder reaction of 6 with 1,3-dimethoxy-1-trimethylsilyloxy-1,
Synthesis of the bisbenzannelated spiroketal core of the γ-rubromycins. The use of a novel Nef-type reaction mediated by Pearlman's catalyst
Capecchi, Tanya,De Koning, Charles B.,Michael, Joseph P.
, p. 2681 - 2688 (2007/10/03)
The synthesis of the bisbenzannelated spiroketal core 6 of γ-rubromycin 1 from the substituted nitrostyrene 20 was achieved by using a novel Nef-type reaction mediated by Pearlman's catalyst. The precursor 28 was synthesised from readily prepared starting materials using Henry condensation chemistry. The product 6 was found to exist in two conformations in solution as shown by NMR spectroscopy.
Nitroalkenes as precursors to the aromatic spiroketal skeleton of γ- rubromycin. A Nef-type reaction mediated by Pearlman's catalyst
Capecchi, Tanya,De Koning, Charles B.,Michael, Joseph P.
, p. 5429 - 5432 (2007/10/03)
The first synthesis of the benzannelated spiroketal core of γ- rubromycin using Henry condensations and a novel Nef-type reaction induced by Pearlman's catalyst is described.
ISOLATION, STRUCTURE AND SYNTHESIS OF MAESANIN, A HOST DEFENSE STIMULANT FROM AN AFRICAN MEDICINAL PLANT MAESA LANCEOLATE
Kubo, Isao,Kim, Mujo,Ganjian, Iraj,Kamikawa, Tadao,Yamagiwa, Yoshiro
, p. 2653 - 2660 (2007/10/02)
The isolation, characterization and an efficient synthesis of maesanin 1, a host defense stimulant isolated from an African medicinal plant Maesa lanceolate, is reported.
ISOLATION, STRUCTURE AND SYNTHESIS OF MAESANIN, A HOST DEFENSE STIMULANT FROM AN AFRICAN MEDICINAL PLANT MAESA LANCEOLATA
Kubo, Isao,Kamikawa, Tadao,Miura, Iwao
, p. 3825 - 3828 (2007/10/02)
The isolation, characterization and an efficient synthesis of maesanin 1, a host defense stimulant isolated from an African medicinal plant Maesa lanceolata is reported.
