Z-selective ring-closing metathesis reactions

A reaction and selection technology, applied in the field of Z-selective closed-loop metathesis reaction, which can solve the problem of high cost

Inactive Publication Date: 2014-05-14
MASSACHUSETTS INST OF TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In most cases, however, macrocyclic RCM proceeds with minimal control over olefinic stereoselectivity; this drawback is

Method used

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  • Z-selective ring-closing metathesis reactions
  • Z-selective ring-closing metathesis reactions
  • Z-selective ring-closing metathesis reactions

Examples

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Embodiment Construction

[0017] 1. Overview of Certain Embodiments of the Invention

[0018] The present invention provides methods for the synthesis of macrocyclic olefins by catalytic RCM reactions, which proceed with high efficiency and stereoselectivity, in some embodiments, up to 97% Z isotropic Construct. Utility was demonstrated by application to the preparation of several bioactive molecules, including the anticancer epothilone A and the antimicrobial nakadomulin A, the synthesis of which had been disrupted by late-stage non-selective RCM. It is demonstrated herein that complexes derived from tungsten or molybdenum provide high efficiency and stereoselectivity, even at relatively high concentrations. The reaction proceeds via the desired pathway rather than the undesired alternative: efficient RCM and cross-metathesis between the incidentally formed self-coupling product and ethylene to regenerate the substrate, but minimal isomerization of macrocyclic Z-olefins.

[0019] Unexpected discover...

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PUM

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Abstract

The present invention relates generally to olefin metathesis. In some embodiments, the present invention provides methods for Z-selective ring-closing metathesis.

Description

[0001] Cross References to Related Applications [0002] This application claims the benefit of U.S. Provisional Application No. 61 / 492,996, filed June 3, 2011, and U.S. Provisional Application No. 61 / 598,307, filed February 13, 2012, the entire contents of each provisional application Incorporated herein by reference. [0003] Statement Regarding Federally Sponsored Research or Development [0004] This invention was made with support under the following government contracts: GM59426 and GM52496, both awarded by the National Institute of Health. The Government has certain rights in this invention. technical field [0005] The present invention generally relates to Z-selective ring-closing metathesis reactions. Background technique [0006] Catalytic olefin metathesis has transformed chemical synthesis and provides an exceptionally efficient route to olefin synthesis. Many bioactive molecules are macrocycles containing alkenes or other commonly occurring functional gr...

Claims

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Application Information

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IPC IPC(8): C07D417/06C07D225/02C07D313/00C07D267/00C07D245/02C07D491/18C07F11/00C07F7/18C07D491/22
CPCC07D225/02C07D245/02C07D267/00C07D313/00C07D417/06C07D498/22C07F7/1804C07F11/00C07B37/10C07D491/18C07D491/22C07D493/04B01J31/2208B01J31/2265B01J31/2278B01J31/2295B01J2231/543B01J2531/64B01J2531/66
Inventor 阿米尔·H·霍维达于苗王辰博理查德·R·施罗克
Owner MASSACHUSETTS INST OF TECH
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