Open AccessTotal Synthesis of (±)-Phaeocaulisin D
Author(s) -
Nameer Ezzat,
Katelyn B Bobek,
Yu Yuan
Publication year - 2020
Publication title -
synlett
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.712
H-Index - 133
eISSN - 1437-2096
pISSN - 0936-5214
DOI - 10.1055/a-1326-9148
Subject(s) - tropone , chemistry , total synthesis , sesquiterpene , rhizome , intramolecular force , stereochemistry , nitric oxide , combinatorial chemistry , organic chemistry , traditional medicine , medicine
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.