Asymmetric Total Synthesis of Kopsiyunnanine K, a Monoterpenoid Indole Alkaloid with a Rearranged Skeleton.
نویسندگان
چکیده
A new monoterpenoid indole alkaloid, kopsiyunnanine K, was isolated from Kopsia arborea. Its intriguing rearranged structure and absolute configuration, which were inferred from spectral data and a possible biosynthetic pathway, were determined on the basis of a 13-step asymmetric total synthesis.
منابع مشابه
Total synthesis of the monoterpenoid alkaloid (±)-tangutorine.
A novel approach to a formal total synthesis of the monoterpenoid indole alkaloid (±)-tangutorine has been developed starting from an α,β-unsaturated cyclic dehydroamino ester. Synthesis of the rather unusual trans-substituted 2,3-indoloquinolizidine substructure was accomplished via Cu(II)-mediated conjugate addition and organozinc/copper coupling as the key steps, thereby setting the stage fo...
متن کاملGluco-indole alkaloids from Nauclea cadamba in Thailand and transformation of 3 alpha-dihydrocadambine into the indolopyridine alkaloid, 16-carbomethoxynaufoline.
Three monoterpenoid gluco-indole alkaloids, 3beta-isodihydrocadambine, cadambine, and 3alpha-dihydrocadambine, were isolated from Nauclea cadamba ROXB. growing in Thailand. The stereochemistry at C19 in 3beta-isodihydrocadambine was elucidated to be R by spectroscopic analysis. Treatment of 3alpha-dihydrocadambine with beta-glucosidase in aqueous ammonium acetate solution gave an indolopyridine...
متن کاملThe Biosynthesis of Monoterpenoid lndole Alkaloids from Strictosidine
The differential incorporation of doubly labelled strictosidine and vincoside into several indole alkaloids belonging to the Corynanthe (3a and 3p series), Aspidosperma, and lboga types in three plant families has been studied, and it has been demonstrated that only strictosidine is incorporated while vincoside is metabolically inert in these plants with regard to alkaloid formation. During the...
متن کاملDetermination of absolute configuration of trimeric indole alkaloid, psychotrimine, by first asymmetric total synthesis.
The first asymmetric total synthesis of psychotrimine, a trimeric indole alkaloid, was accomplished via an asymmetric Ireland-Claisen rearrangement to construct a chiral quaternary carbon center, thereby establishing the absolute configuration of psychotrimine.
متن کاملEnantioselective total synthesis of (+)-ibophyllidine via an asymmetric phosphine-catalyzed [3 + 2] annulation.
In this study we performed the total synthesis of the terpene indole alkaloid (+)-ibophyllidine through a pathway involving asymmetric phosphine catalysis, with our novel l-4-hydroxyproline-derived chiral phosphine mediating the key [3 + 2] annulation. Hydrogenation of the [3 + 2] adduct allowed the rapid formation of the stereochemically dense pyrrolidine ring of (+)-ibophyllidine in excellent...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید
ثبت ناماگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید
ورودعنوان ژورنال:
- Organic letters
دوره 18 14 شماره
صفحات -
تاریخ انتشار 2016