Synthesis of Polyfunctional Drimanes from Drim-7,9(11)-diene and Drim-8-en-7-one

Using Singlet Oxygen to Synthesize Natural Products and Drugs

“…Butenolides have been extensively studied in batch reactions of 1 O 2 . For example, observations that singlet oxygen reacts with furans to produce butenolides and spiroketal natural products was an important discovery. − Much synthetic utility has been found; one example of a batch reaction is shown in Scheme . Here, the synthesis of a tetraquinane oxa-cage bislactone structure in (±)-parasecolide 325 occurred from the MB-sensitized photooxidation of furan 323 at 0 °C .…”

Safe and Fast Flow Synthesis of Functionalized Oxazoles with Molecular Oxygen in a Microstructured Reactor

“…By applying mild conditions with gold­(I) catalysis, generating alkylideneoxazolines, and in situ converting it with molecular oxygen, the oxazole core is built up and immediately functionalized to efficiently form hydroperoxymethyl oxazoles in an atom-economic and green process . The hydroperoxymethyl group offers potential for multifunctional conversions by reduction, rearrangements, or follow-up reactions . Contrary to other methods that use, e.g., hypervalent iodine reagents or pyridine/quinoline N -oxides as oxidizing agents in the formation of oxazoles, the direct oxidation with molecular oxygen and introduction of a versatile functionality in one step is very convenient and conforms to the pursuit of atom economy.…”

Synthesis of Novel Tetranorlabdane Derivatives with Unprecedented Carbon Skeleton

“…4 So far, several syntheses of tetranorlabdanes have been performed based on ketoester 6. 5,9,12 This paper reports the continuation of our investigations 14,15 into the chemistry of (-)-sclareol (1) and describes new regio-and stereoselective syntheses of polyfunctional tetranorlabdanes (homodrimanes) starting from methyl 7oxo-13,14,15,16-tetranorlabd-8-en-12-oate (6).…”

“…In view of this, based on (-)-sclareol (1) and its derivative (+)-sclareolide (2), syntheses of important drimane sesquiterpenoids and some tetranorlabdanes have been performed via methyl bicyclohomofarnesoates 3-5 and methyl 7-oxo-13,14,15,16-tetranorlabd-8-en-12-oate (6, Figure 1). [3][4][5][6][7][8][9][10][11][12][13][14][15] Syntheses of tetranorlabdanes are generally shorter and easier than those of the related drimanes. Some of them have been applied on an industrial scale because the resulting tetranorlabdanes are used in perfumery, cosmetics, and tobacco products.…”