Reductive thioalkylation of a pyranonaphthoquinone

Authors
Brimble, MA Nairn, MR
Citation
Ma. Brimble et Mr. Nairn, Reductive thioalkylation of a pyranonaphthoquinone, J CHEM S P1, (3), 2000, pp. 317-322
Citations number
32
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
ISSN journal
0300922X → ACNP
Issue
3
Year of publication
2000
Pages
317 - 322
Database
ISI
SICI code
0300-922X(2000):3<317:RTOAP>2.0.ZU;2-#
Abstract
Reduction of pyranonaphthoquinone 6 with sodium dithionite in the presence of the sulfur nucleophiles thiocresol, phenylmethanethiol and butanethiol a fforded the thioalkylated products 7 and 8, 9 and 10, and 11 and 12 respect ively. This observed reductive thioalkylation at C-4 supports the postulate that naturally occurring pyranonaphthoquinone antibiotics may act as biore ductive alkylating agents.