A novel approach in drug discovery: Synthesis of estrone-talaromycin natural product hybrids

ISSN
0947-6539
Date Issued
2000
Author(s)
Schneider, G.
Wolfling, J.
Fecher, A.
Nobel, T.
Schuberth, I.
Wulff, C.
DOI
10.1002/1521-3765(20001016)6:20<3755::AID-CHEM3755>3.3.CO;2-C
Abstract
Hetero-Diels - Alder reaction of the steroidal exocyclic enol ethers 14 and 15, obtained from the secoestrones 8 and 9 by reduction, iodoetherification, and elimination, with ethyl O-benzoyldiformylacetate (16) leads to the spiroacetals 17 and 18 as a mixture of four diastereomers. Reduction of the major diastereomers 17a and 18 a with DIBAH and subsequent hydrogenation yields the novel natural product hybrids 21, 23, 24, and 25, which possess the structural features of the steroid estrone (7) and the mycotoxin talaromycin 6.