115-61-7Relevant academic research and scientific papers
Biomimetic Synthesis of Chaxine and its Related Compounds
Niki, Misaki,Hirata, Yushi,Nakazaki, Atsuo,Wu, Jing,Kawagishi, Hirokazu,Nishikawa, Toshio
, p. 4848 - 4860 (2020)
The highly oxidized natural products chaxine B and BB have been synthesized from ergosterol in eight steps according to a route inspired by their proposed biosynthesis; key steps were an oxidative cascade from a furan intermediate to an enol ester using m-chloroperbenzoic acids (MCPBA), followed by diastereoselective epoxidation and acyloxy migration. This concise synthesis resulted in the revision of the structures of chaxine B and its naturally occurring analogs and syntheses of the unnatural analogues of these natural products for biological investigations.
Biomimetic Synthesis and Structural Revision of Chaxine B and Its Analogues
Hirata, Yushi,Nakazaki, Atsuo,Kawagishi, Hirokazu,Nishikawa, Toshio
supporting information, p. 560 - 563 (2017/02/10)
Chaxine B and its analogues were synthesized from ergosterol in eight steps on the basis of our proposed biosynthetic pathway, which includes a highly site-selective and regioselective Baeyer-Villiger oxidation as the key step. This synthesis enabled the revision of the structures of chaxine B and its analogues.
STEREOCHEMICAL ASPECTS OF THE FORMATION OF TOXISTEROLS A
Orlov, A. I.,Mikhailova, N. P.,B'yunov, K. A.
, p. 193 - 196 (2007/10/02)
Mechanisms for the formation of toxisterol A are suggested.The connection between the conformation of the initial previtamin and the stereochemistry of the reaction products is discussed.
