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Formal syntheses of (±)-Asterisca-3(15),6-diene and (±)-Pentalenene using Rh(I)-catalyzed [(5+2)+1] cycloaddition
- Source :
-
Tetrahedron . Jun2009, Vol. 65 Issue 24, p4709-4713. 5p. - Publication Year :
- 2009
-
Abstract
- Abstract: Efficient formal syntheses of (±)-Asterisca-3(15),6-diene, a natural product with a bicyclo[6.3.0]undecane skeleton, and (±)-Pentalenene, a natural product with a tricyclo[6.3.0.04,8]undecane skeleton, have been achieved by using Rh(I)-catalyzed [(5+2)+1] cycloaddition. The [(5+2)+1] reaction provides an expeditious approach to reach the bicyclic cyclooctenone 4, which was quickly transformed (via hydroboration then oxidation) to diketone 14, a key advanced intermediate for the total synthesis of (±)-Asterisca-3(15),6-diene. Through further transformations, 14 was converted to diene 18, an advanced intermediate for the total synthesis of (±)-Pentalenene. [Copyright &y& Elsevier]
Details
- Language :
- English
- ISSN :
- 00404020
- Volume :
- 65
- Issue :
- 24
- Database :
- Academic Search Index
- Journal :
- Tetrahedron
- Publication Type :
- Academic Journal
- Accession number :
- 39780179
- Full Text :
- https://doi.org/10.1016/j.tet.2009.04.020