Stereodivergent Attached-Ring Synthesis via Non-Covalent Interactions: A Short Formal Synthesis of Merrilactone A.

Cyclization Lactones / chemical synthesis Molecular Structure Sesquiterpenes / chemical synthesis Stereoisomerism
Michael addition attached-ring diastereoselectivity natural products synthesis design

Journal

Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543

Informations de publication

Date de publication:
17 01 2022
Historique:
received: 26 10 2021
pubmed: 26 11 2021
medline: 22 2 2022
entrez: 25 11 2021
Statut: ppublish

Résumé

A strategy to control the diastereoselectivity of bond formation at a prochiral attached-ring bridgehead is reported. An unusual stereodivergent Michael reaction relies on basic vs. Lewis acidic conditions and non-covalent interactions to control re- vs. si- facial selectivity en route to fully substituted attached-rings. This divergency reflects differential engagement of one rotational isomer of the attached-ring system. The successful synthesis of an erythro subtarget diastereomer ultimately leads to a short formal synthesis of merrilactone A.

Identifiants

DOI: 10.1002/anie.202114514 PMID: 34820990 PMC: PMC8748398
pubmed: 34820990
doi: 10.1002/anie.202114514
pmc: PMC8748398
mid: NIHMS1759733
doi:

Substances chimiques

Lactones 0
Sesquiterpenes 0
merrilactone A 0

Types de publication

Journal Article Research Support, N.I.H., Extramural Research Support, Non-U.S. Gov't Research Support, U.S. Gov't, Non-P.H.S.

Langues

eng

Sous-ensembles de citation

IM

Pagination

e202114514

Subventions

Organisme : Division of Chemistry
ID : CHE-1856747
Organisme : Division of Chemistry
ID : CHE-1764328
Organisme : NIGMS NIH HHS
ID : GM122606
Pays : United States
Organisme : NIGMS NIH HHS
ID : R35 GM122606
Pays : United States
Organisme : Division of Chemistry
ID : GRFP
Organisme : Japan Society for the Promotion of Science

Informations de copyright

© 2021 Wiley-VCH GmbH.

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Auteurs

Benjamin J Huffman (BJ)

Department of Chemistry, Scripps Research, 10550 North Torrey Pines Road, La Jolla, CA, 92037, USA.

Tiffany Chu (T)

Department of Chemistry, Scripps Research, 10550 North Torrey Pines Road, La Jolla, CA, 92037, USA.

Yusuke Hanaki (Y)

Department of Chemistry, Scripps Research, 10550 North Torrey Pines Road, La Jolla, CA, 92037, USA.

Jonathan J Wong (JJ)

Department of Chemistry and Biochemistry, UCLA: University of California Los Angeles, 619 Charles E. Young Drive East, Los Angeles, CA, 90095, USA.

Shuming Chen (S)

Department of Chemistry and Biochemistry, Oberlin College, 119 Woodland Street, Oberlin, OH, 44074, USA.

Kendall N Houk (KN)

Department of Chemistry and Biochemistry, UCLA: University of California Los Angeles, 619 Charles E. Young Drive East, Los Angeles, CA, 90095, USA.

Ryan A Shenvi (RA)

Department of Chemistry, Scripps Research, 10550 North Torrey Pines Road, La Jolla, CA, 92037, USA.
ORCID: 0000-0001-8353-6449

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Classifications MeSH

questionsmedicales.fr › Métabolisme › Cyclisation › Stereodivergent Attached-Ring Synthesis via...
questionsmedicales.fr › Composés chimiques organiques › Lactones › Stereodivergent Attached-Ring Synthesis via...
questionsmedicales.fr › Phénomènes chimiques › Structure moléculaire › Stereodivergent Attached-Ring Synthesis via...
questionsmedicales.fr › Composés chimiques organiques › Hydrocarbures › Terpènes › Sesquiterpènes › Stereodivergent Attached-Ring Synthesis via...
questionsmedicales.fr › Phénomènes chimiques › Phénomènes de chimie organique › Isomérie › Stéréoisomérie › Stereodivergent Attached-Ring Synthesis via...