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Traceless Solid‐Phase Synthesis of Cyclopenta[ c ]quinolines and Cyclopenta[ c ]chromenes via Hetero [6+3] Cycloadditions of Fulvene. A Facile Approach to the 11‐Heterosteroids Framework
Author(s) -
Hong BorCherng,
Chen ZhongYi,
Chen WeiHung,
Sun HsuI,
Lee GeneHsiang
Publication year - 2005
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.200500028
Subject(s) - fulvene , chemistry , fulvenes , cycloaddition , stereochemistry , medicinal chemistry , organic chemistry , catalysis
Abstract The hetero [6+3] cycloaddition of fulvenes to benzoquinones and iodoanilines provides an efficient route to the synthesis of cyclopenta[ c ]‐4H‐chromen‐8‐ol, benzo[ d ]cyclopenta[ e ]‐3H‐3‐azin‐8‐ol and other 11‐hetero steroids. The structure of the cyclopenta[ c ]chromene skeleton was confirmed by the X‐ray structure analysis of the p ‐bromobenzoate of 39 . A small library consisting of 110 examples was prepared by reacting benzoquinones or iodoanilines with resin 17 .