Synthesis of a C(1)–C(23) Fragment for Spirastrellolide E: Development of a Mechanistic Rationale for Spiroketalization

[Image: see text] Synthetic analysis of spirastrellolide E envisioned to entail a cross-metathesis union of the northern and southern hemispheres followed by a Sharpless epoxidation/methylation sequence to achieve the C(22,23) stereogenicity leads to the design of a C(1)–C(23) advanced southern hemi...

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Autores principales: Sokolsky, Alexander, Cattoen, Martin, Smith, Amos B.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2015
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4450744/
https://www.ncbi.nlm.nih.gov/pubmed/25844543
http://dx.doi.org/10.1021/acs.orglett.5b00595
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author Sokolsky, Alexander
Cattoen, Martin
Smith, Amos B.
author_facet Sokolsky, Alexander
Cattoen, Martin
Smith, Amos B.
author_sort Sokolsky, Alexander
collection PubMed
description [Image: see text] Synthetic analysis of spirastrellolide E envisioned to entail a cross-metathesis union of the northern and southern hemispheres followed by a Sharpless epoxidation/methylation sequence to achieve the C(22,23) stereogenicity leads to the design of a C(1)–C(23) advanced southern hemisphere exploiting a gold-catalyzed directed spiroketalization as a key step. Stereochemical analysis of this strategic transformation provides insight on the impact of the directing group carbinol stereogenicity on the reaction efficiency and, in turn, permits the conversion of the minor isomer of the spiroketal precursor to the requisite congener for successful spiroketalization.
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spelling pubmed-44507442016-04-06 Synthesis of a C(1)–C(23) Fragment for Spirastrellolide E: Development of a Mechanistic Rationale for Spiroketalization Sokolsky, Alexander Cattoen, Martin Smith, Amos B. Org Lett [Image: see text] Synthetic analysis of spirastrellolide E envisioned to entail a cross-metathesis union of the northern and southern hemispheres followed by a Sharpless epoxidation/methylation sequence to achieve the C(22,23) stereogenicity leads to the design of a C(1)–C(23) advanced southern hemisphere exploiting a gold-catalyzed directed spiroketalization as a key step. Stereochemical analysis of this strategic transformation provides insight on the impact of the directing group carbinol stereogenicity on the reaction efficiency and, in turn, permits the conversion of the minor isomer of the spiroketal precursor to the requisite congener for successful spiroketalization. American Chemical Society 2015-04-06 2015-04-17 /pmc/articles/PMC4450744/ /pubmed/25844543 http://dx.doi.org/10.1021/acs.orglett.5b00595 Text en Copyright © 2015 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Sokolsky, Alexander
Cattoen, Martin
Smith, Amos B.
Synthesis of a C(1)–C(23) Fragment for Spirastrellolide E: Development of a Mechanistic Rationale for Spiroketalization
title Synthesis of a C(1)–C(23) Fragment for Spirastrellolide E: Development of a Mechanistic Rationale for Spiroketalization
title_full Synthesis of a C(1)–C(23) Fragment for Spirastrellolide E: Development of a Mechanistic Rationale for Spiroketalization
title_fullStr Synthesis of a C(1)–C(23) Fragment for Spirastrellolide E: Development of a Mechanistic Rationale for Spiroketalization
title_full_unstemmed Synthesis of a C(1)–C(23) Fragment for Spirastrellolide E: Development of a Mechanistic Rationale for Spiroketalization
title_short Synthesis of a C(1)–C(23) Fragment for Spirastrellolide E: Development of a Mechanistic Rationale for Spiroketalization
title_sort synthesis of a c(1)–c(23) fragment for spirastrellolide e: development of a mechanistic rationale for spiroketalization
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4450744/
https://www.ncbi.nlm.nih.gov/pubmed/25844543
http://dx.doi.org/10.1021/acs.orglett.5b00595
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