Ti(II) and Rh(I) Complexes as Reagents toward a Thapsigargin Core | Zendy

Youssouf Sanogo | Zendy; Raja Ben Othman | Zendy; Sabrina Dhambri | Zendy; Mohamed Selkti | Zendy; Alan Jeuken | Zendy; Joëlle Prunet | Zendy; JeanPierre Férézou | Zendy; Janick Ardisson | Zendy; MarieIsabelle Lannou | Zendy; Geoffroy Sorin | Zendy

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Ti(II) and Rh(I) Complexes as Reagents toward a Thapsigargin Core

Author(s) -

Youssouf Sanogo,

Raja Ben Othman,

Sabrina Dhambri,

Mohamed Selkti,

Alan Jeuken,

Joëlle Prunet,

JeanPierre Férézou,

Janick Ardisson,

MarieIsabelle Lannou,

Geoffroy Sorin

Publication year - 2019

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/acs.joc.8b03249

Subject(s) - chemistry , thapsigargin , serca , stereochemistry , bicyclic molecule , enyne , reagent , alcohol , intramolecular force , combinatorial chemistry , intramolecular reaction , calcium , catalysis , organic chemistry , atpase , enzyme

A novel approach toward the [5-7]fused bicyclic core of thapsigargin, a subnanomolar inhibitor of the endo/sarcoplasmic calcium ATPase (SERCA), is presented. The synthetic route includes an original Ti(II)-mediated hydroxy-directed reductive coupling of an enantiomerically enriched propargylic alcohol and an intramolecular Rh(I)-catalyzed cyclocarbonylation reaction as key steps. Interestingly, through the first experiments of titanocene-mediated reductive cyclization of a 1,8-enyne, a seven-membered cycle was isolated as a unique product with a total diastereoselectivity.

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