Hafeman NJ,
Loskot SA,
Reimann CE,
Pritchett BP,
Virgil SC,
Stoltz BM.
California Institute of Technology, Pasadena, USA
The Total Synthesis of (–)-Scabrolide A.
J. Am. Chem. Soc. 2020;
142: 8585-8590
Key words
(–)-scabrolide A - norcembranoid diterpenoid - Diels–Alder reaction - hydrosilylation
- [2+2] cycloaddition - Tamao–Fleming oxidation - Grieco elimination - oxidative fragmentation/
elimination
Significance
Stoltz and co-workers report the first total synthesis of (–)-scabrolide A, a norcembranoid
diterpenoid isolated from soft coral Sinularia scabra. The target compound inhibits production of IL-6 and IL-12 and therefore holds promise
as anti-inflammatory agent. The fused [5,6,7]-scaffold features six stereogenic centers.
Comment
The authors employ a convergent route which couples two fragments derived from the
chiral pool by esterification. Diels–Alder reaction and [2+2] cycloaddition generate
a [5,6,4,5]-scaffold which is then elaborated to the target compound by an oxidative
fragmentation/elimination.
