203314-50-5Relevant articles and documents
Asymmetric Total Synthesis of Hetidine-Type C20-Diterpenoid Alkaloids: (+)-Talassimidine and (+)-Talassamine
Zhang, Quanzheng,Yang, Zhao,Wang, Qi,Liu, Shuangwei,Zhou, Tao,Zhao, Yankun,Zhang, Min
, p. 7088 - 7095 (2021)
Here, we report the first asymmetric total synthesis of (+)-talassimidine and (+)-talassamine, two hetidine-type C20-diterpenoid alkaloids. A highly regio- and diastereoselective 1,3-dipolar cycloaddition of an azomethine ylide yielded a chiral tetracyclic intermediate in high enantiopurity, thus providing the structural basis for asymmetric assembly of the hexacyclic hetidine skeleton. In this key step, the introduction of a single chiral center induces four new continuous chiral centers. Another key transformation is the dearomative cyclopropanation of the benzene ring and subsequent SN2-like ring opening of the resultant cyclopropane ring with water as a nucleophile, which not only establishes the B ring but also precisely installs the difficult-to-achieve equatorial C7-OH group.
Iron and copper salts in the synthesis of benzo[b]furans
Bonnamour, Julien,Piedrafita, Maria,Bolm, Carsten
supporting information; experimental part, p. 1577 - 1581 (2010/09/05)
Intramolecular C-O bond forming reactions of aryl 2-bromobenzyl ketones lead to benzo[b]furans. The cyclizations can be catalyzed by 10 mol% of iron trichloride (of 98% or of 99.995% purity) or sub-mol% quantities of copper(II) chloride (of 99.995% purity
Synthesis of pyrazolo[1,5-a]indoles via copper(I)-catalyzed intramolecular amination
Zhu, Yong-Ming,Qin, Lie-Na,Liu, Rui,Ji, Shun-Jun,Katayama, Hajime
, p. 6262 - 6266 (2008/02/10)
A variety of pyrazolo[1,5-a]indole derivatives were synthesized via Cu(I)-catalyzed intramolecular amination reactions. This novel method provides a general and efficient synthesis to indoles fused with pyrazole rings in high yields.