SYNTHESIS OF NEW CONDURITOL ANALOGS DERIVED FROM BICYCLOOCTATRIENE - BIS-HOMO-CONDURITOL-D AND BIS-HOMO-CONDURITOL-F

Authors
KARA Y BALCI M BOURNE SA WATSON WH
Citation
Y. Kara et al., SYNTHESIS OF NEW CONDURITOL ANALOGS DERIVED FROM BICYCLOOCTATRIENE - BIS-HOMO-CONDURITOL-D AND BIS-HOMO-CONDURITOL-F, Tetrahedron letters, 35(20), 1994, pp. 3349-3352
Citations number
10
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
35
Issue
20
Year of publication
1994
Pages
3349 - 3352
Database
ISI
SICI code
0040-4039(1994)35:20<3349:SONCAD>2.0.ZU;2-J
Abstract
The first synthesis of conduritol analogues 2 and 3 is reported. The k ey compound 7 reacted with KMnO4 and m-chloroperbenzoic acid in a ster eospecific manner to give syn-addition products 9 and 10, respectively . Zinc-dust elimination of 10 followed by epoxide opening resulted in the formation of 3b. The free tetrol 3 was obtained by ammonolysis. Th e other tetrol isomer 2 was obtained by similar synthetic steps.