1. A short synthesis of the aromatic monoterpene espintanol
- Author
-
David J. Wadsworth and Sabine Losch
- Subjects
Oxandra espintana ,Chemistry ,Monoterpene ,Organic Chemistry ,chemistry.chemical_element ,Alcohol ,Biochemistry ,chemistry.chemical_compound ,Methyl Ketone ,Yield (chemistry) ,Drug Discovery ,Organic chemistry ,Rearrangement reaction ,Lithium - Abstract
A flexible and expedient synthesis of the leishmanicidal and trypanocidal monoterpene espintanol 1 , first isolated in 1991 from the spruce Oxandra espintana , was achieved in seven steps and with an overall yield of 11%. Key steps were the direct conversion of the methyl ester 6b to the methyl ketone 7 upon treatment with methyl lithium and the acid-catalyzed benzylic hydroperoxide rearrangement reaction of the secondary alcohol 11 to afford 1 .
- Published
- 1994