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

نویسندگان

  • Shuyu Chu
  • Niels Münster
  • Tudor Balan
  • Martin D Smith
چکیده

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) a cascade ene-yne-ene ring closing metathesis to forge the tetracyclic morphine core. This approach enables a short and stereoselective synthesis of morphine in an overall yield of 6.6 %.

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

Optimal Synthesis of a Cascade Refrigeration System of LNG Through MINLP Model for Pure Refrigerant Cycles

 liquefied natural gas (LNG) is the most economical way of transporting natural gas (NG) over long distances. Liquefaction of NG by using vapor compression refrigeration system requires high operating and capital cost. Due to lack of systematic design methods for multistage refrigeration cycles, the conventional approaches of determining optimal cycle configuration are mostly based on trial-an...

متن کامل

Optimal Synthesis of Cascade Refrigeration in Liquefied Natural Gas Cycles by Pinch-Exergy

Iran’s vast common natural gas resources and the necessity to extract and export it as Liquefied Natural Gas (LNG) to distances more than 3000Km opens a lucrative field for researchers to optimize LNG cycles. In this article heat integration in cryogenic cycles by determining interacycle partition temperature and optimizing refrigeration features like Subcooler, Presaturator, aftercooler, reboi...

متن کامل

Total synthesis of seco-lateriflorone

A convergent strategy toward the synthesis of lateriflorone (5) is described. Our approach is based on biosynthetic considerations and draws on a sequence of prenylation, oxygenation and Claisen reactions for the construction of chromenequinone 6, and a tandem Claisen/Diels–Alder reaction cascade for the synthesis of caged tricycle 7. Union of fragments 6 and 7 led to the synthesis of secolater...

متن کامل

Bioinspired total synthesis of (±)-yezo'otogirin C.

The first and protective group-free total synthesis of (±)-yezo'otogirin C has been achieved from 3-methyl-4-prenylcyclohex-2-enone in eight steps with 23% overall yield. The tricyclic core of (±)-yezo'otogirin C was established via a bioinspired oxidative cascade cyclization strategy using Mn(II)/Mn(III) and O2, followed by reduction of the peroxy-bridged intermediate using thiourea in refluxi...

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:

دوره 55  شماره 

صفحات  -

تاریخ انتشار 2016