Abstract
A convergent total synthesis of peloruside A (1) is described. The key strategic features are a diastereoselective lactonization to generate a C5-C9 valerolactone from the C2-symmetric ketone 4, which comprises C1–C9 of 1, and a relay ring closing metathesis (RRCM) reaction to produce a dehydrovalerolactone 20, which embodies C13–C19. A new isomer of 1, the valerolactone iso-peloruside A (iso-1), was identified.
Publication types
-
Research Support, N.I.H., Extramural
MeSH terms
-
Biological Products / chemical synthesis
-
Biological Products / chemistry
-
Bridged Bicyclo Compounds, Heterocyclic / chemical synthesis*
-
Bridged Bicyclo Compounds, Heterocyclic / chemistry
-
Cyclization
-
Dicarboxylic Acids / chemistry
-
Kinetics
-
Lactones / chemical synthesis
-
Lactones / chemistry*
-
Stereoisomerism
Substances
-
Biological Products
-
Bridged Bicyclo Compounds, Heterocyclic
-
Dicarboxylic Acids
-
Lactones
-
peloruside A
-
azelaic acid