Total Syntheses of Microcladallenes A, B, and C

  • Author: Shaun Scally
  • Published Date: 02 October 2015
  • Source / Publisher: Chemistry – A European Journal/Wiley-VCH
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
thumbnail image: Total Syntheses of Microcladallenes A, B, and C

Related Societies

Microcladallenes A, B, and C are natural products that have previously been isolated from the red algae Laurencia microcladia. Proposed structures of compounds A and C have been suggested based on proton and carbon NMR spectroscopy, whereas an absolute configuration of compound B has been confirmed using X-ray crystallography.


Deukjoon Kim, Seoul National University, Republic of Korea, and colleagues have accomplished the substrate-controlled asymmetric total syntheses of (+)-microcladallenes A, B, and C based on the proposed structures. The syntheses of A and B confirmed the structures and absolute configurations of both natural products. However, the synthesis of C, which includes seven stereogenic centers and an (R)-bromoallene in its compact C15 framework, revealed that its proposed structure must be revised.


X-ray crystallographic analysis coupled with chemical transformations strongly suggested that the originally proposed structure of C was incorrect, so an unambiguous structure assignment needs a future reisolation and analysis of the natural product.


 

Article Views: 1784

Sign in Area

Please sign in below

Additional Sign In options

Please note that to comment on an article you must be registered and logged in.
Registration is for free, you may already be registered to receive, e.g., the newsletter. When you register on this website, please ensure you view our terms and conditions. All comments are subject to moderation.

Article Comments - To add a comment please sign in

Bookmark and Share

If you would like to reuse any content, in print or online, from ChemistryViews.org, please contact us first for permission. more


CONNECT:

ChemistryViews.org on Facebook

ChemistryViews.org on Twitter ChemistryViews.org on YouTube ChemistryViews.org on LinkedIn Sign up for our free newsletter


A product of ChemPubSoc Europe (16 European Chemical Societies)and Wiley-VCH