Synthetic studies on pentacyclic aromatic alkaloids, kuanoniamine A, 11-hydroxyascididemin, and neocalliactine acetate

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,...

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Published inTetrahedron Vol. 53; no. 50; pp. 17029 - 17038
Main Authors Kitahara, Yoshiyasu, Nakahara, Shinsuke, Yonezawa, Takanobu, Nagatsu, Masanori, Shibano, Yoshikazu, Kubo, Akinori
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 15.12.1997
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ASCIDIDEMIN
TUNICATE
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Summary: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). Pentacyclic aromatic alkaloids, kuanoniamine A and 11-hydroxyascididemin were synthesized. The structure of neocalliactine acetate was determined to be 3-acetoxyascididemin by direct synthesis.
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(97)10153-3