Synthesis of (-)-morphine.

نویسندگان

  • Douglass F Taber
  • Timothy D Neubert
  • Arnold L Rheingold
چکیده

The preparation of the diastereomerically pure beta-tetralone ketal 4 is reported. Intramolecular alkylidene C-H insertion followed by hydrolysis of 4 proceeded to give the enantiomerically pure cyclopentene 15. The key step in this synthesis was the bis-intramolecular cyclization of keto aldehyde 2 to give the tetracyclic intermediate 20. Enone 20 was converted over several steps to (-)-morphine 1.

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

منابع مشابه

Characterization and DFT Studies for Green Synthesis of Silver Nanoparticles by Morphine Ampules and their Anti-proliferation Activity

This study is a green approach for the synthesis of silver nanoparticles (AgNPs) using morphine ampoules (MO) as reducing and capping agents. The toxicity effects of prepared particles were evaluated using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay on breast cancer cells. The spherical AgNPs with the average size of 50nm were synthesized and studied by UV–visible s...

متن کامل

A Cascade Strategy Enables a Total Synthesis of (±)‐Morphine

Morphine has been a target for synthetic chemists since Robinson proposed its correct structure in 1925, resulting in a large number of total syntheses of morphine alkaloids. Here we report a total synthesis of (±)-morphine that employs two key strategic cyclizations: 1) a diastereoselective light-mediated cyclization of an O-arylated butyrolactone to form a tricyclic cis-fused benzofuran and 2...

متن کامل

Short, asymmetric synthesis of epi-morphine ACNO analogues.

A concise and efficient asymmetric synthesis of ACNO analogues of morphine is reported.

متن کامل

The immunosuppressive effects of chronic morphine treatment are partially dependent on corticosterone and mediated by the mu-opioid receptor.

Wild-type and mu-opioid receptor knockout (MORKO) mice were used to investigate the role of corticosterone (CORT) and the mu-opioid receptor (MOR) in chronic morphine-mediated immunosuppression. We found that although plasma CORT concentrations in CORT infusion (10 mg/kg/day) and morphine-pellet implantation (75 mg) mice were similar (400-450 ng/ml), chronic morphine treatment resulted in a sig...

متن کامل

Acute and chronic morphine treatment and the hydroxylation of (1-14C)-L-tyrosine in the mouse brain.

Tyrosine hydroxylase activity in slices of caudate nucleus was increased by morphine (100 mg/kg i.p.) administered to naive mice. During chronic treatment with morphine tolerance developed to this effect and 36 h after the final chronic morphine injection there was a decrease in enzyme activity in this area. There was no change in tyrosine hydroxylase activity in slices of diencephalon, brainst...

متن کامل

ذخیره 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 نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

عنوان ژورنال:
  • Journal of the American Chemical Society

دوره 124 42  شماره 

صفحات  -

تاریخ انتشار 2002