71572-60-6Relevant academic research and scientific papers
Application of tandem ring-closing enyne metathesis: Formal total synthesis of (-)-cochleamycin A
Mukherjee, Sumit,Lee, Daesung
, p. 2916 - 2919 (2009)
A tandem ring-closing metathesis of a silaketal-based dlenyne substrate proceeded efficiently to provide a bicyclic siloxane, which upon removal of the silicon tether afforded an (E,Z)-1,3-dienediol. Further manipulation of this key functional motif rende
SYNTHESIS OF HALICHONDRINS
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Paragraph 00861, (2019/01/21)
The present invention provides methods for the synthesis of ketones involving a Ni/Zr-mediated coupling reaction. The Ni/Zr-mediated ketolization reactions can be used in the synthesis of halichondrins (e.g., halichondrin A, B, C; homohalichondrin A, B, C; norhalichondnn A, B, C), and analogs thereof. Therefore, the present invention also provides synthetic methods useful for the synthesis of halichondrins, and analogs thereof. Also provided herein are compounds (i.e., intermediates) useful in the synthesis of halichondrins, and analogs thereof. In particular, the present invention provides methods and compounds useful in the synthesis of compound of Formula (H3-A)
Synthesis and Isolation of Organogold Complexes through a Controlled 1,2-Silyl Migration
McGee, Philippe,Bellavance, Gabriel,Korobkov, Ilia,Tarasewicz, Anika,Barriault, Louis
, p. 9662 - 9665 (2015/06/30)
During our efforts toward the synthesis of naturally occurring polyprenylated polycyclic acylphloroglucinol using a AuI-catalyzed 6-endo dig carbocyclization, we isolated stable vinyllic gold intermediates. Optimization lead to isolated yields of up to 98 %, using 2-(di-tert-butylphosphino)biphenyl as the ligand. This transformation is derived from a silyl rearrangement that can be fully controlled according to the nature of the substituent on the ynone. This selective transformation does not require basic conditions to prevent protodeauration. These vinylgold complexes are the first isolated intermediates during a silyl migration with gold(I). More than 16 new organogold complexes were synthesized and characterized by single-crystal X-ray diffraction. Reactivity of these complexes is also presented.
Copper-Catalyzed Propargylic Substitution of Dichloro Substrates: Enantioselective Synthesis of Trisubstituted Allenes and Formation of Propargylic Quaternary Stereogenic Centers
Li, Hailing,Grassi, David,Guénée, Laure,Bürgi, Thomas,Alexakis, Alexandre
supporting information, p. 16694 - 16706 (2016/02/12)
An easy and versatile Cu-catalyzed propargylic substitution process is presented. Using easily prepared prochiral dichloro substrates, readily available Grignard reagents together with catalytic amount of copper salt and chiral ligand, we accessed a range of synthetically interesting trisubstituted chloroallenes. Substrate scope and nucleophile scope are broad, providing generally high enantioselectivity for the desired 1,3-substitution products. The enantioenriched chloroallenes could be further transformed into the corresponding trisubstituted allenes or terminal alkynes bearing all-carbon quaternary stereogenic centers, through the copper-catalyzed enantiospecific 1,1/1,3-substitutions. The two successive copper-catalyzed reactions could be eventually combined into a one-pot procedure and different desired allenes or alkynes were obtained respectively with high enantiomeric excesses.
