Synthesis of Ambrox® from (−)-sclareol and (+)-cis-abienol

Bifunctional cis-Abienol Synthase from Abies balsamea Discovered by Transcriptome Sequencing and Its Implications for Diterpenoid Fragrance Production

“…Among other applications, cis-abienol 4 and other oxygen-containing diterpenoids of plant origin (e.g. sclareol and manool) are important in the fragrance industry to produce Ambrox, which serves as a sustainable replacement for the use of ambergris in high end perfume formulations (7). Whereas Ambrox is produced from plant terpenoids, ambergris is an animal product secreted from the intestines of sperm whales, which are listed as an endangered species.…”

Oxidative Degradations of the Side Chain of Unsaturated Ent-labdanes. Part II

“…From 2D HSQC spectrum, H-17a and H-17b showed correlations with a carbon atom at δ 50.4 ppm, assigned to C-17, whereas in the 2D HMBC spectrum, H-17a and H-17b showed 3 J correlations with C-9 (δ 50.4 ppm), with C-7 (δ 35.9 ppm) and 2 J with a quaternary carbon atom at δ 58.2 ppm, assigned to C-8 (see Figure 1a). The α-sterochemistry of the oxirane ring methylene group (C-17) was inferred mainly from gs-sel-1 H 1D-NOESY experiments: when H-17a was selectively irradiated, long range interactions (strong) with the Me-20 group (0.87 ppm) and H-11a (1.07 ppm) were observed, whereas H-17b only showed long range interactions (medium) with H-7α (1.82 ppm) and Me-20 group (see Figure 1b).…”

“…Diterpenoids with labdanic structures are a very important natural source of hydrocarbon skeletons which have been used in the elaboration of a great number of drimane compounds with remarkable biological properties, among which their olfactory [1][2][3], antifeedant [4], antimicrobial, cytotoxic [5], growth regulator [6], herbicidal and insecticidal activities [7][8][9][10] may be mentioned.…”

Oxidative Degradations of the Side Chain of Unsaturated Ent-labdanes. Part I.

“…Degradation of the side chain of the mixture of compounds 1a-2a using either the OsO 4 /NaIO 4 or RuCl 3 /NaIO 4 systems, a degradation used previously for compounds with similar structures [1][2][3]14], led to the formation of compounds 5 and 6 (Scheme 1). Nevertheless, when the mixture 1a-2a was treated with the RuCl 3 /NaIO 4 system, a greater yield of compound 5 was obtained (76% v/s 68% with OsO 4 /NaIO 4 system).…”

“…Diterpenoids with labdanic structures are a very important natural source of hydrocarbon skeletons which have been used in the elaboration of a great number of drimane compounds with remarkable biological properties, among which their olfactory [1][2][3], antifeedant [4], antimicrobial, cytotoxic [5], growth regulator [6], herbicidal and insecticidal activities [7][8][9][10] may be mentioned.…”