Synthesis and absolute stereochemistry of roseophilin

Authors
Harrington, PE Tius, MA
Citation
Pe. Harrington et Ma. Tius, Synthesis and absolute stereochemistry of roseophilin, J AM CHEM S, 123(35), 2001, pp. 8509-8514
Citations number
35
Categorie Soggetti
Chemistry & Analysis",Chemistry
Journal title
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
ISSN journal
00027863 → ACNP
Volume
123
Issue
35
Year of publication
2001
Pages
8509 - 8514
Database
ISI
SICI code
0002-7863(20010905)123:35<8509:SAASOR>2.0.ZU;2-6
Abstract
The enantiospecific total synthesis of natural roseophilin has been complet ed in 7.0% overall yield over 15 steps by means of an asymmetric cyclopenta nnelation. This establishes the absolute configuration of the natural produ ct as 22R,23R. Cyclopentenone (+)-12 was prepared in 78% yield and 86% ee i n the key step.