Total synthesis of the CP-molecules (CP-263,114 and CP-225,917, phomoidrides B and A). 2. Model studies for the construction of key structural elements and first-generation strategy.
نویسندگان
چکیده
Crucial model synthetic and mechanistic studies directed toward the development of methodology for the construction of the maleic anhydride moiety of the CP-molecules are described. Studies directed toward the stereoselective attachment of the upper side chain, culminating in the discovery of long-range stereochemical control, are also discussed. In addition, a first-generation strategy toward the CP-molecules, establishing key intermediate 5 as a "beachhead" from which all future operations would diverge, is also presented. Although this first-generation strategy failed to yield the target molecules, the endeavor laid the important groundwork for the next-generation drives toward the CP-molecules.
منابع مشابه
Total synthesis of the CP-molecules (CP-263,114 and CP-225,917, phomoidrides B and A). 1. Racemic and asymmetric synthesis of bicyclo[4.3.1] key building blocks.
A brief introduction into the chemistry of the CP-molecules is followed by first-generation synthetic sequences toward key building blocks for their total synthesis. Processes for both racemic and enantiomerically enriched bicyclo[4.3.1] ketone 6 or its equivalent are described, and the absolute stereochemistries of the optically enriched intermediates are determined. The efficient route develo...
متن کاملTotal synthesis of the CP-molecules (CP-263,114 and CP-225,917, phomoidrides B and A). 3. Completion and synthesis of advanced analogues.
The completion of the total syntheses of the CP-molecules is reported. Several strategies and tactics, including the use of amide-based protecting groups for the homologated C-29 carboxylic acid and the use of an internal pyran protecting group scheme, are discussed. The endeavors leading to the design of new methods for the homologation of hindered aldehydes and to the isolation of a polycycli...
متن کاملCP-225,917 and CP-263,114, novel Ras farnesylation inhibitors from an unidentified fungus. I. Taxonomy, fermentation, isolation, and biochemical properties.
During the course of our screening for squalene synthase inhibitors and Ras farnesylation inhibitors, a novel fungal culture was discovered to produce two structurally unique compounds, CP-225,917 and CP-263,114, as well as zaragozic acid A (squalestatin I). The two compounds are characterized by a bicyclo[4.3.1]dec-1,6-diene core plus two extended alkyl chains. CP-225,917 and CP-263,114 inhibi...
متن کاملStrategic Competence and Foreign Language test Performance in Iranian Context
A number of studies have accounted the integral role of foreign/second language learning and learner strategy use. However, a few of these studies have considered the relationships between strategic competence and its use and foreign language performance (FLP). This study applied structural equation modeling to deeply investigate the relationships between test takers’ strategy use and their per...
متن کاملStrategic Competence and Foreign Language test Performance in Iranian Context
A number of studies have accounted the integral role of foreign/second language learning and learner strategy use. However, a few of these studies have considered the relationships between strategic competence and its use and foreign language performance (FLP). This study applied structural equation modeling to deeply investigate the relationships between test takers’ strategy use and their per...
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:
- Journal of the American Chemical Society
دوره 124 10 شماره
صفحات -
تاریخ انتشار 2002