Back to Search
Start Over
Silver-catalyzed benzannulation, part 2: Total synthesis of (1R,4S,11S)-8,19-dihydroxyserrulat-14-ene and (1R,4S,11S)-8-hydroxyserrulat-14-en-19-oic acid.
- Source :
-
ARKIVOC: Online Journal of Organic Chemistry . 2022, Vol. 2022, p188-204. 17p. - Publication Year :
- 2022
-
Abstract
- This paper reports the total synthesis of the serrulatane natural products (1R,4S,11S)-8,19-dihydroxyserrulat-14-ene (5.0% yield) and (1R,4S,11S)-8-hydroxyserrulat-14-en-19-oic acid (3.8% yield) via a silver-catalyzed 6-endo-dig benzannulation of an (-)-isopulegol derived ene-yne-ol in 17 steps. Analysis of the spectroscopic data as well as the specific rotations allowed for the confirmation of the stereochemistry at C1, C4 and C11 as (1R,4S,11S) for both natural products 8,19-dihydroxyserrulat-14-ene and 8-hydroxyserrulat-14-en-19-oic acid that were reported from the Australian desert plant, Eremophila neglecta. [ABSTRACT FROM AUTHOR]
- Subjects :
- *ANNULATION
*NATURAL products
*DESERT plants
*ACIDS
*STEREOCHEMISTRY
*DATA analysis
Subjects
Details
- Language :
- English
- ISSN :
- 15517004
- Volume :
- 2022
- Database :
- Academic Search Index
- Journal :
- ARKIVOC: Online Journal of Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 161149258
- Full Text :
- https://doi.org/10.24820/ark.5550190.p011.815