10064-16-1Relevant articles and documents
ZnI2/Zn(OTf)2-TsOH: A versatile combined-Acid system for catalytic intramolecular hydrofunctionalization and polyene cyclization
Chou, Ting-Hung,Yu, Bo-Hung,Chein, Rong-Jie
supporting information, p. 13522 - 13525 (2019/11/14)
A mild and efficient combined-Acid system using a zinc(ii) salt [ZnI2 or Zn(OTf)2] and p-Toluene sulfonic acid (TsOH) was investigated for catalytic cationic cyclizations, including intramolecular hydrocarboxylation, hydroalkoxylation, hydroamination, hydroamidation, hydroarylation and polyene cyclizations. This reaction provides easy access to five-and six-membered O-and N-containing saturated heterocyclic compounds, tetrahydronaphthalene derivatives and polycyclic skeletons in excellent yield with perfect Markovnikov selectivity and under mild conditions. The operational simplicity, broad applicability, and use of inexpensive commercially available catalysts make this protocol superior to existing methodologies.
Highly enantioselective proton-initiated polycyclization of polyenes
Surendra, Karavadhi,Corey
supporting information; experimental part, p. 11992 - 11994 (2012/09/08)
This report describes the synthesis of a range of chiral polycyclic molecules (tricyclic to pentacyclic) from achiral polyene precursors by enantioselective proton-initiated polycyclization promoted by the 1:1 complex of o,o′-dichloro-BINOL and SbCl5. Excellent yields (ca. 90% per ring formed) and enantioselectivety (20:1 to 50:1) were obtained. The process is practical as well as efficient, because the chiral ligand is both readily prepared from R,R- or S,S-BINOL and easily recovered from the reaction mixture by extraction.
Stereoselective intramolecular 6-exo-Heck reaction : A facile synthetic route to podocarpa-8,11,13-triene and diterpenoid resin acids intermediates
Mukhopadhyaya, Jayanta K.,Ghosh, Ajit K.,Ghatak, Usha Ranjan
, p. 835 - 837 (2007/10/03)
Intramolecular Heck reaction of the olefins 1a-c in the presence of sodium formate affords ca 3:1 mixtures of the respective trans- and cis-octahydrophenanthrenes 3a-c and 4a-c. Similar reaction of the olefmic ester 2 provides a 70:30 mixture of (±)-methyl desisopropyldehydroabietate 6 and (±)10-epi-methyl desoxypodocarpate 7.