Total Synthesis of (-)-Batrachotoxinin A: A Local-Desymmetrization Approach.

Batrachotoxins / chemical synthesis Molecular Structure Oxidation-Reduction Stereoisomerism

Journal

Journal of the American Chemical Society
ISSN: 1520-5126
Titre abrégé: J Am Chem Soc
Pays: United States
ID NLM: 7503056

Informations de publication

Date de publication:
26 02 2020
Historique:
pubmed: 11 2 2020
medline: 7 1 2021
entrez: 11 2 2020
Statut: ppublish

Résumé

An enantioselective total synthesis of (-)-batrachotoxinin A is accomplished based on a key photoredox coupling reaction and the subsequent local-desymmetrization operation. After the expedient assembly of the highly oxidized steroid skeleton, a delicate sequence of redox manipulations was carried out to deliver a late-stage intermediate on gram scale-and ultimately (-)-batrachotoxinin A in an efficient manner.

Identifiants

DOI: 10.1021/jacs.9b12882 PMID: 32036656
pubmed: 32036656
doi: 10.1021/jacs.9b12882
doi:

Substances chimiques

Batrachotoxins 0

Types de publication

Journal Article Research Support, Non-U.S. Gov't

Langues

eng

Sous-ensembles de citation

IM

Pagination

3675-3679

Auteurs

Yinliang Guo (Y)

Key Laboratory of Bioorganic Chemistry and Molecular Engineering, Ministry of Education and Beijing National Laboratory for Molecular Science, College of Chemistry and Molecular Engineering , Peking University , Beijing 100871 , China.

Zhixian Guo (Z)

Key Laboratory of Bioorganic Chemistry and Molecular Engineering, Ministry of Education and Beijing National Laboratory for Molecular Science, College of Chemistry and Molecular Engineering , Peking University , Beijing 100871 , China.

Jia-Tian Lu (JT)

Key Laboratory of Bioorganic Chemistry and Molecular Engineering, Ministry of Education and Beijing National Laboratory for Molecular Science, College of Chemistry and Molecular Engineering , Peking University , Beijing 100871 , China.
ORCID: 0000-0002-0824-2552

Runting Fang (R)

Key Laboratory of Bioorganic Chemistry and Molecular Engineering, Ministry of Education and Beijing National Laboratory for Molecular Science, College of Chemistry and Molecular Engineering , Peking University , Beijing 100871 , China.

Si-Cong Chen (SC)

Key Laboratory of Bioorganic Chemistry and Molecular Engineering, Ministry of Education and Beijing National Laboratory for Molecular Science, College of Chemistry and Molecular Engineering , Peking University , Beijing 100871 , China.

Tuoping Luo (T)

Key Laboratory of Bioorganic Chemistry and Molecular Engineering, Ministry of Education and Beijing National Laboratory for Molecular Science, College of Chemistry and Molecular Engineering , Peking University , Beijing 100871 , China.
Peking-Tsinghua Center for Life Sciences, Academy for Advanced Interdisciplinary Studies , Peking University , Beijing 100871 , China.
ORCID: 0000-0003-2156-3198

Articles similaires

A molecular mechanism for bright color variation in parrots.

Roberto Arbore, Soraia Barbosa, Jindich Brejcha et al.
1.00
Animals Feathers Pigmentation Parrots Aldehyde Dehydrogenase

Use of dislodgeable foliar residue studies for the evaluation of isomerization potential of active substances for non-dietary risk assessment.

Silke Wagner, Christian J Kuster
1.00
Risk Assessment Plant Leaves Isomerism Humans Stereoisomerism

Tumor-targeted glutathione oxidation catalysis with ruthenium nanoreactors against hypoxic osteosarcoma.

Hanchen Zhang, Nicolás Montesdeoca, Dongsheng Tang et al.
1.00
Osteosarcoma Animals Glutathione Oxidation-Reduction Mice

Reducing the mitochondrial oxidative burden alleviates lipid-induced muscle insulin resistance in humans.

Matteo Fiorenza, Johan Onslev, Carlos Henríquez-Olguín et al.
1.00
Humans Insulin Resistance Muscle, Skeletal Oxidative Stress Oxidation-Reduction

Classifications MeSH

questionsmedicales.fr › Facteurs biologiques › Toxines biologiques › Venins › Venins d'amphibien › Batrachotoxines › Total Synthesis of (-)-Batrachotoxinin A: A...
questionsmedicales.fr › Phénomènes chimiques › Structure moléculaire › Total Synthesis of (-)-Batrachotoxinin A: A...
questionsmedicales.fr › Métabolisme › Métabolisme énergétique › Oxydoréduction › Total Synthesis of (-)-Batrachotoxinin A: A...
questionsmedicales.fr › Phénomènes chimiques › Phénomènes de chimie organique › Isomérie › Stéréoisomérie › Total Synthesis of (-)-Batrachotoxinin A: A...