Intramolecular alkylative arylation of oxabicylic alkene: a potential diene approach for the synthesis of estrone and analogous steroid structures.
Regioselective and stereospecific intramolecular alkylative arylation of unsaturated oxabicyclic diol 6, mediated by Lewis acid or strong protic acid to give the tetracyclic products 7a and 7b, as shown above, represents the first example of an electrophilic (cationic in character) ring-opening-cyclization of oxabicyclic alkene. This constitutes the key cyclization step for a long-standing and potentially useful diene approach for the synthesis of estrone and analogous steroid structures. [structure: see text]
Li
Wei-Dong Z
WD
National Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, China. wdli@fas.harvard.edu
Wei
Kun
K
D000466:Alkadienes / Q000737:chemistry*; D000478:Alkylation; D001643:Bridged Bicyclo Compounds / Q000737:chemistry*; D003500:Cyclization; D004970:Estrone / Q000138:chemical synthesis* / Q000494:pharmacology; D015394:Molecular Structure; D013237:Stereoisomerism; D013256:Steroids / Q000737:chemistry*
D000466:Alkadienes; D001643:Bridged Bicyclo Compounds; D013256:Steroids; D004970:Estrone