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Synfacts 2020; 16(07): 0749
DOI: 10.1055/s-0040-1707009
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (–)-Scabrolide A

Contributor(s):
Erick M. Carreira
,
Patrick Pfaff
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
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Further Information

Publication History

Publication Date:
17 June 2020 (online)

 
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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.


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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.


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