Facile Access to Optically Active Ring C Aromatic Diterpene Derivatives from (+)-Manool. First Synthesis of 13,14-Dihydroxy-8,11,13-podocarpatrien-7-one

作者：Novoa Maria L; Salazar Franklin J; Gamez Carlos; Angarita Ana Y; Tropper Eleonora; Canudas Nieves; Villamizar Jose E^*

来源：Natural Product Communications, 2014, 9(3): 355-358.

DOI：10.1177/1934578x1400900317

• Podocarpane
• Abietane
• Diterpenes
• Nimbidiol
• 7-Deoxynimbidiol
• (+)-Manool
• Synthesis

14,15,17-Trinorlabdan-8,13-dione 6 was efficiently synthesized via ozonolysis of (+)-manool (4) followed by treatment with aqueous NaOH in the presence of tetra-n-butylammonium bromide as catalyst. This protocol has the advantages of high yield, mild conditions and simple procedure. Utilizing this strategy, the first enantiospecific synthesis of 13,14-dihydroxy-8,11,13-podocarpatrien-7-one (1), a constituent of Taiwania cryptomerioides and Celastrus paniculatus, was achieved starting from (+)-manool (4) after a four-step sequence in 24% overall yield.

• 出版日期2014-3