Synthesis of Patchouli Alcohol

Chasing Molecules That Were Never There: Misassigned Natural Products and the Role of Chemical Synthesis in Modern Structure Elucidation

“…Before World War II, a chemist would have relied almost exclusively on the art of chemical synthesis, primarily in the form of degradation and derivatization reactions, to develop and test structural hypotheses in a process that often took years to complete when grams of material were available. [8] As shown in Scheme 1 a, those operations were: 1) epoxidation of the double bond in 7 followed by nucleophilic ring opening to generate diol 9; 2) acetylation of the resulting secondary alcohol; 3) thermally induced elimination of the newly formed acetate; and 4) hydrogenation of the resulting olefin. In fact, it could be argued that the characterization of natural products has become a routine task, one which no longer even requires a reaction flask!…”

Immunomodulatory Potential of Patchouli Alcohol Isolated from <i>Pogostemon cablin</i> (Blanco) Benth (Lamiaceae) in Mice

“…Statistical significances within a parameter were evaluated by one-way and multiple analysis of variation (ANOVA), where significant differences (as shown in the plots) indicated as */ # for p < 0.05, and more significant **/ ## for p < 0.01. [18][19][20][21][22][23]. The purity of PA was 99.3% as indicated by GC analysis (Figure 1).…”

From Vetiver to Patchouli: Discovery of a NewHigh‐Impact Spirocyclic Patchouli Odorant

“…Already a few years later, however, Büchi et al [4] proved Treibs's structure 1 wrong, and proposed structure 2. This was even proven by a total synthesis [5] starting from homocamphor. Thus, there was considerable astonishment when the X-ray crystal structure [6] of the chromate of (-)-patchoulol (3) was not in agreement with structure 2: A Wagner-Meerwein rearrangement in the course of the peracid oxidation had led to the correct structure of (-)-patchoulol (3) without having been noticed in the synthetic work.…”