Bidirectional cross metathesis and ring-closing metathesis/ring opening of a C(2)-symmetric building block: a strategy for the synthesis of decanolide natural products

Starting from the conveniently available ex-chiral pool building block (R,R)-hexa-1,5-diene-3,4-diol, the ten-membered ring lactones stagonolide E and curvulide A were synthesized using a bidirectional olefin-metathesis functionalization of the terminal double bonds. Key steps are (i) a site-selecti...

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Detalles Bibliográficos
Autores principales: Schmidt, Bernd, Kunz, Oliver
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2013
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3869341/
https://www.ncbi.nlm.nih.gov/pubmed/24367418
http://dx.doi.org/10.3762/bjoc.9.289
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author Schmidt, Bernd
Kunz, Oliver
author_facet Schmidt, Bernd
Kunz, Oliver
author_sort Schmidt, Bernd
collection PubMed
description Starting from the conveniently available ex-chiral pool building block (R,R)-hexa-1,5-diene-3,4-diol, the ten-membered ring lactones stagonolide E and curvulide A were synthesized using a bidirectional olefin-metathesis functionalization of the terminal double bonds. Key steps are (i) a site-selective cross metathesis, (ii) a highly diastereoselective extended tethered RCM to furnish a (Z,E)-configured dienyl carboxylic acid and (iii) a Ru–lipase-catalyzed dynamic kinetic resolution to establish the desired configuration at C9. Ring closure was accomplished by macrolactonization. Curvulide A was synthesized from stagonolide E through Sharpless epoxidation.
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spelling pubmed-38693412013-12-23 Bidirectional cross metathesis and ring-closing metathesis/ring opening of a C(2)-symmetric building block: a strategy for the synthesis of decanolide natural products Schmidt, Bernd Kunz, Oliver Beilstein J Org Chem Full Research Paper Starting from the conveniently available ex-chiral pool building block (R,R)-hexa-1,5-diene-3,4-diol, the ten-membered ring lactones stagonolide E and curvulide A were synthesized using a bidirectional olefin-metathesis functionalization of the terminal double bonds. Key steps are (i) a site-selective cross metathesis, (ii) a highly diastereoselective extended tethered RCM to furnish a (Z,E)-configured dienyl carboxylic acid and (iii) a Ru–lipase-catalyzed dynamic kinetic resolution to establish the desired configuration at C9. Ring closure was accomplished by macrolactonization. Curvulide A was synthesized from stagonolide E through Sharpless epoxidation. Beilstein-Institut 2013-11-18 /pmc/articles/PMC3869341/ /pubmed/24367418 http://dx.doi.org/10.3762/bjoc.9.289 Text en Copyright © 2013, Schmidt and Kunz https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Schmidt, Bernd
Kunz, Oliver
Bidirectional cross metathesis and ring-closing metathesis/ring opening of a C(2)-symmetric building block: a strategy for the synthesis of decanolide natural products
title Bidirectional cross metathesis and ring-closing metathesis/ring opening of a C(2)-symmetric building block: a strategy for the synthesis of decanolide natural products
title_full Bidirectional cross metathesis and ring-closing metathesis/ring opening of a C(2)-symmetric building block: a strategy for the synthesis of decanolide natural products
title_fullStr Bidirectional cross metathesis and ring-closing metathesis/ring opening of a C(2)-symmetric building block: a strategy for the synthesis of decanolide natural products
title_full_unstemmed Bidirectional cross metathesis and ring-closing metathesis/ring opening of a C(2)-symmetric building block: a strategy for the synthesis of decanolide natural products
title_short Bidirectional cross metathesis and ring-closing metathesis/ring opening of a C(2)-symmetric building block: a strategy for the synthesis of decanolide natural products
title_sort bidirectional cross metathesis and ring-closing metathesis/ring opening of a c(2)-symmetric building block: a strategy for the synthesis of decanolide natural products
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3869341/
https://www.ncbi.nlm.nih.gov/pubmed/24367418
http://dx.doi.org/10.3762/bjoc.9.289
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