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Title: Total Synthesis of Chalaniline A: An Aminofulvene Fused Chromone from Vorinostat-Treated Fungus Chalara sp. 6661
Chalaniline A, an aminofulveno[1,2-b]chromone derivative previously isolated from a vorinostat-treated ascomycete Chalara sp., was prepared in nine steps from orcinol (3,5- dihydroxytoluene). In a key transformation, the tricyclic ring system of the target was generated by a pyrrolidine-catalyzed double annulation between α-(methylsulfinyl)-2,6-dihydroxy-4-methylacetophenone and the ketaldoester, methyl 2,5-dioxopentanoate. The resulting tertiary alcohol (coniochaetone H) was further converted to chalaniline A by operations including dehydration (to yield a hydroxyfulvene), Vilsmeier reaction, and enamine exchange.  more » « less
Award ID(s):
2247031
PAR ID:
10575117
Author(s) / Creator(s):
; ; ; ; ;
Publisher / Repository:
American Chemical Society
Date Published:
Journal Name:
The Journal of Organic Chemistry
Volume:
89
Issue:
19
ISSN:
0022-3263
Page Range / eLocation ID:
14601 to 14605
Format(s):
Medium: X
Sponsoring Org:
National Science Foundation
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