Journal
JOURNAL OF NATURAL PRODUCTS
Volume 82, Issue 1, Pages 9-15Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.jnatprod.8b00129
Keywords
-
Funding
- Junta de Andalucia [P08-FQM-3596]
- Ministerio de Economia y Competitividad [CTQ2015-64049-C3-3-R]
Ask authors/readers for more resources
The first total synthesis of a natural diterpene valparane, (-)-valpara-2,15-diene (1), has been achieved from all-trans-geranylgeraniol (9), a natural renewable compound. The key steps involve a Ti(III)-mediated radical cyclization of the chiral monoepoxypolyene (14R,1SR)-14,15-epoxy,16-tert-butyldimethylsilyloxygeranyllinalyl acetate (8) to give the 6,6,7-tricyclic intermediate 7 with stereocontrolled formation of six stereocenters; a stereo- and regio-directed contraction of the A ring in 7 to produce a cyclopentane ring; and the ready generation of the target isopropenyl group. This research provides access to structurally related natural products such as the sesquiterpene (+)-isodaucene (3), the synthesis of which is also reported herein.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available