Synthesis and natural occurrence of (Z/E)-β-and γ-curcumen-12-ol

Abstract

Abstract:(Z/E)-β-Curcumen-12-ol (Z/E)-(1) was synthesized via Birch reduction of acid 6 starting from α-curcumene (5). An olefin isomerization of 1 is the key step in the synthesis of (Z/E)-γ-curcumen-12-ol (Z/E)-(2). Sesquiterpene alcohol (E)-1 was found for the first time in nature as a minor constituent of different Santalum species by using the synthetic sample as reference.

Characterization of a Sesquiterpene Synthase Catalyzing Formation of Cedrol and Two Diastereoisomers of Tricho-Acorenol from Euphorbia fischeriana

“…These five compounds were extracted and isolated, and their structures were elucidated. Compound 1 is indeed cedrol, as its NMR data and specific rotation value ([α] 22 D +11.6, c 0.3, CH 2 Cl 2 ) are identical with the reported data of cedrol. , Compound 5 was determined as ( E )-β-curcumen-12-ol by comparing its MS (Figure c) and NMR data with the literature data, as well.…”

“…Compound 1 is indeed cedrol, as its NMR data and specific rotation value ([α] 22 D +11.6, c 0.3, CH 2 Cl 2 ) are identical with the reported data of cedrol. 21,22 Compound 5 was determined as (E)-β-curcumen-12-ol by comparing its MS (Figure 2c) and NMR data with the literature data, 23 1). Fifteen carbon signals were preliminarily assigned by the 13 1).…”

Eastern Polynesian Sandalwood Oil (Santalum insulare Bertero ex A. DC.) – a Detailed Investigation

“…Sample C had a lower amount of (Z)-α-and β-santalol and a significantly higher (Z)-nuciferol content in comparison to A and B. Moreover, nuciferol related compounds, like (Z)-β-and γ-curcumen-12-ol [9], (E)-nuciferol and nuciferal were present either in higher amounts or exclusively found in C [10]. In our case, these differences cannot be linked to either the use of different plant materials or extraction techniques, which can also cause such variations in the oil composition [11].…”

Natural sesquiterpenoids

“…One of these synthetic sesquiterpenes, (E)-bcurcumen-12-ol 94, was identified for the first time in nature as a minor constituent of different Santalum species. 85 An enantiospecific synthesis of (+)-hernandulcin has been achieved. 86 The synthesis and stereochemical determination of an antifeeding bisabolane sesquiterpene 95 has been described.…”