Concise synthesis of 22-hydroxyacuminatine, cytotoxic camptothecinoid from Camptotheca acuminata, by pyridone benzannulation.
نویسندگان
چکیده
A short, efficient synthesis of 22-hydroxyacuminatine, starting from a readily accessible hydroxy pyridone, is presented; key steps include a Heck coupling with methyl pentadienoate, a flash vacuum pyrolytic cyclization, and a Friedländer condensation.
منابع مشابه
Genetic Diversity in Camptotheca Decaisne
RAPD markers were used to reveal the genetic diversity of the genus Camptotheca. Three primers (OPA02, OPA03, and OPA04), generating 44 polymorphic bands using randomly amplified polymorphic DNA (RAPD) markers, were able to discriminate among 25 Camptotheca populations. The band size varied from 268-4,411bp, with an average of 15 bands/primer. Of these populations, cultivars ‘Katie’ (KT) and ‘A...
متن کاملTissue-specific expression of the beta-subunit of tryptophan synthase in Camptotheca acuminata, an indole alkaloid-producing plant.
Camptothecin is an anticancer drug produced by the monoterpene indole alkaloid pathway in Camptotheca acuminata. As part of an investigation of the camptothecin biosynthetic pathway, we have cloned and characterized a gene from C. acuminata encoding the beta-subunit of tryptophan (Trp) synthase (TSB). In C. acuminata TSB provides Trp for both protein synthesis and indole alkaloid production and...
متن کاملDesign, synthesis, and biological evaluation of 14-substituted aromathecins as topoisomerase I inhibitors.
The aromathecin or "rosettacin" class of topoisomerase I (top1) inhibitors is effectively a "composite" of the natural products camptothecin and luotonin A and the synthetic indenoisoquinolines. The aromathecins have aroused considerable interest following the isolation and total synthesis of 22-hydroxyacuminatine, a rare cytotoxic natural product containing the 12 H-5,11a-diazadibenzo[ b, h]fl...
متن کاملMolecular cloning, characterization and expression of a jasmonate biosynthetic pathway gene encoding allene oxide cyclase from Camptotheca acuminata.
AOC (allene oxide cyclase; EC 5.3.99.6), an essential enzyme in jasmonic acid and its methyl ester biosynthesis, was cloned from Camptotheca acuminata (named as CaAOC), a native medicinal plant species in China. CaAOC had significant similarity at the amino-acid level with AOCs from other plant species. Comparison between the sequences of the full-length cDNA and genomic DNA of CaAOC revealed t...
متن کاملEvaluation of antimicrobial activity of endophytic fungi from Camptotheca acuminata (Nyssaceae).
Agricultural research of plant-derived endophytic fungi has grown in recent decades. We isolated 26 endophytic fungi from the leaves, stems and fruits of "the tree of life", Camptotheca acuminata, and tested them for antimicrobial activities based on growth inhibition measurements in a modified agar diffusion method. Fermentation broths from most of the isolates exhibited antifungal activity an...
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 & biomolecular chemistry
دوره 4 3 شماره
صفحات -
تاریخ انتشار 2006