General Approach to the Synthesis of the Chlorosulfolipids Danicalipin A, Mytilipin A, and Malhamensilipin A in Enantioenriched Form

A second-generation synthesis of three structurally related chlorosulfolipids has been developed. Key advances include highly stereocontrolled additions to α,β-dichloroaldehydes, kinetic resolutions of complex chlorinated vinyl epoxide intermediates, and Z-selective alkene cross metatheses of cis...

Celý popis

Uloženo v:

Podrobná bibliografie
Vydáno v:	Journal of organic chemistry Ročník 79; číslo 5; s. 2226 - 2241
Hlavní autoři:	Chung, Won-jin, Carlson, Joseph S, Vanderwal, Christopher D
Médium:	Journal Article
Jazyk:	angličtina
Vydáno:	WASHINGTON American Chemical Society 07.03.2014 Amer Chemical Soc
Témata:	Chemistry Chemistry, Organic Kinetics Lipids - chemical synthesis Lipids - chemistry Molecular Structure Physical Sciences Science & Technology Stereoisomerism Vinyl Compounds - chemistry MICROBIAL SULFOLIPIDS CROSS-METATHESIS ENANTIOSELECTIVE SYNTHESIS ABSOLUTE-CONFIGURATION KINETIC RESOLUTION SILICON TETRACHLORIDE OLEFIN METATHESIS STEREOSELECTIVE ACCESS RUTHENIUM METATHESIS CATALYSTS LEWIS-BASE
ISSN:	0022-3263, 1520-6904, 1520-6904
On-line přístup:	Získat plný text
Tagy:	Přidat tag Žádné tagy, Buďte první, kdo vytvoří štítek k tomuto záznamu!

Popis
Shrnutí:	A second-generation synthesis of three structurally related chlorosulfolipids has been developed. Key advances include highly stereocontrolled additions to α,β-dichloroaldehydes, kinetic resolutions of complex chlorinated vinyl epoxide intermediates, and Z-selective alkene cross metatheses of cis-vinyl epoxides. This strategy facilitated the synthesis of enantioenriched danicalipin A, mytilipin A, and malhamensilipin A in nine, eight, and 11 steps, respectively.
Bibliografie:	NIH RePORTER ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	0022-3263 1520-6904 1520-6904
DOI:	10.1021/jo5000829