77239-50-0Relevant articles and documents
Synthesis of natural (?)-antrocin and its enantiomer via stereoselective aldol reaction
Angamuthu, Venkatachalam,Tai, Dar-Fu
, (2020/02/25)
The total synthesis of (?)-antrocin and its enantiomer are presented. Antrocin (?)-1 is an important natural product which acts as an antiproliferative agent in a metastatic breast cancer cell line (IC50: 0.6 μM). The key features of this synthesis are: (a) selective anti-addition of trimethylsilyl cyanide (TMSCN) to α,β-unsaturated ketone; (b) resolution of (±)-7 using chiral auxiliary L-dimethyl tartrate through formation of cyclic ketal diastereomers followed by simple column chromatography separation and acid hydrolysis; (c) substrate-controlled stereoselective aldol condensation of (+)-12 with monomeric formaldehyde and pyridinium chlorochromate (PCC) oxidation for synthesis of essential lactone core in (?)-14; and (d) non-basic Lombardo olefination of the carbonyl at the final step to yield (?)-antrocin. In addition, (+)-9 cyclic ketal diastereomer was converted to (+)-antrocin with similar reaction sequences.
SYNTHESIS OF (+/-)-α-AMBRINOL
Takazawa, Osamu,Tamura, Hiroshi,Kogami, Kunio,Hayashi, Kazuo
, p. 1257 - 1258 (2007/10/02)
Synthesis of α-ambrinol was successfully accomplished by cyclization of dihydro-γ-ionone ethylene acetal which was prepared by the titanium(IV)-promoted reaction of 3,3-dimethyl-1-trimethylsiloxycyclohexene with methyl vinyl ketone ethylene acetal followed by exomethylenation with triphenylphosphonium methylide.
