Synlett 2021; 32(07): 689-692
DOI: 10.1055/a-1326-9148
letter

Total Synthesis of (±)-Phaeocaulisin D

Nameer Ezzat
a   Department of Chemistry, University of Central Florida, 4111 Libra Drive, Orlando, Florida 32816, USA
b   Department of Chemistry, College of Education, University of Mosul, Mosul 41002, Iraq
,
Katelyn Bobek
a   Department of Chemistry, University of Central Florida, 4111 Libra Drive, Orlando, Florida 32816, USA
,
Yu Yuan
a   Department of Chemistry, University of Central Florida, 4111 Libra Drive, Orlando, Florida 32816, USA
› Author Affiliations

Support was provided by the National Institute of General Medical Sciences (1R15GM12068501). A student fellowship was provided by the Iraqi Ministry of High Education and Scientific Research.


Abstract

The tropone sesquiterpene phaeocaulisin D, isolated from the rhizomes of Curcuma phaeocaulis, has previously been shown to inhibit nitric oxide production in macrophages. A total synthesis of phaeocaulisin D was accomplished by using an intramolecular cyclization–dearomatization as a key step. The highlights of the synthesis are effective formation of the 5–7 fused tropone system, and selective methylation of a late-stage intermediate.

Supporting Information



Publication History

Received: 12 November 2020

Accepted: 01 December 2020

Accepted Manuscript online:
01 December 2020

Article published online:
05 January 2021

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