Premium
A Novel Oxidative Cleavage of the Steroidal Skeleton
Author(s) -
Jautelat Rolf,
MüllerFahrnow Anke,
Winterfeldt Ekkehard
Publication year - 1999
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/(sici)1521-3765(19990401)5:4<1226::aid-chem1226>3.0.co;2-6
Subject(s) - hydroxylation , oxidative cleavage , chemistry , cleavage (geology) , dihydroxylation , stereochemistry , alcohol , steric effects , oxidative phosphorylation , bond cleavage , organic chemistry , biochemistry , enantioselective synthesis , catalysis , biology , enzyme , paleontology , fracture (geology)
The unusual bisketal 2 is afforded by a novel oxidative cleavage of the steroidal skeleton of homoallylic alcohol 1 . This cleavage reaction was discovered during synthetic studies towards higher oxygenated cephalostatin analogues in which Shing's flash‐hydroxylation technique was used for the β‐diastereoselective syn ‐dihydroxylation of the sterically hindered Δ 14, 15 ‐double bond in homoallylic alcohol 1 . By using this synthetic pathway, the synthesis of highly oxygenated bissteroidal pyrazines could be achieved. The latter, however, showed no tumor‐inhibiting properties in preliminary tests.