133401-10-2Relevant academic research and scientific papers
Synthetic studies on pentacyclic aromatic alkaloids, kuanoniamine A, 11-hydroxyascididemin, and neocalliactine acetate
Kitahara, Yoshiyasu,Nakahara, Shinsuke,Yonezawa, Takanobu,Nagatsu, Masanori,Shibano, Yoshikazu,Kubo, Akinori
, p. 17029 - 17038 (2007/10/03)
A pentacyclic aromatic alkaloid, kuanoniamine A (6) was synthesized in three steps from 6-methoxybenzothiazole-4,7-dione (8) and 2-aminoacetophenone (9). 11-Hydroxyascididemin (4) was prepared from 5,8-quinolinedione (13, 14) or 1,4-acridinedione (20). The structure of neocalliactine acetate, a derivative of calliactine, was determined to be 5 by total synthesis from 6-methoxy-5,8-quinolinedione (28) and 2-amino-5-methoxyacetophenone (29).
Efficient and convenient pyridine ring-e formation of the cytotoxic marine alkaloid ascididemin and related analogues
Lindsay, Brent S.,Pearce, A. Norrie,Copp, Brent R.
, p. 2587 - 2592 (2007/10/03)
Abstract Conversion of tetracyclic quinone 1 to the cytotoxic pentacyclic alkaloid ascididemin (2) in 80% yield is achieved by reaction with paraformaldehyde and ammonium chloride in refluxing acetic acid. High yielding annelations are also observed for the related analogues N-8 deaza ascididemin (3) and kuanoniamine A (4).
TOTAL SYNTHESIS OF KUANONIAMINE A, 11-HYDROXYASCIDIDEMIN, AND NEOCALLIACTINE ACETATE
Kitahara, Yoshiyasu,Nakahara, Shinsuke,Yonezawa, Takanobu,Nagatsu, Masanori,Kubo, Akinori
, p. 943 - 946 (2007/10/02)
A pentacyclic aromatic alkaloid, kuanoniamine A (5) was synthesized from 6-methoxybenzothiazole-4,7-dione (7) and 2-aminoacetophenone (8).Similarly, 11-hydroxyascididemin (4) was prepared from 6-bromo-4-chloro-5,8-dimethoxyquinoline (12).The structure of neocalliactine acetate, a derivative of calliactine, was determined as 19 by total synthesis from 6-methoxy-5,8-quinolinedione (23) and 2-amino-5-methoxyacetophenone (24).
