Efficient Synthesis of an Enantiopure Thiasteroid by a Double Heck Reaction

2004 ◽  
Vol 57 (7) ◽  
pp. 635 ◽  
Author(s):  
Lutz F. Tietze ◽  
Lars P. Lücke ◽  
Felix Major ◽  
Peter Müller
Keyword(s):  
Heck Reaction ◽  
Efficient Synthesis ◽  
Heck Reactions ◽  
Thiophene Derivatives ◽  
Intramolecular Heck Reaction

The thiaestrane 7 was synthesized by two sequential Heck reactions starting from the thiophene derivatives 8a–8c, which contain a (Z)-halogenovinyl group, and the enantiopure hydrindene 2a. The first intermolecular Pd-catalyzed reaction leads to 11a and 11b in a highly regio- and diastereoselective manner. A subsequent intramolecular Heck reaction catalyzed by the palladacycle 4 then gave the thiasteroid 7 with an unusual cis-junction of the rings B and C.

scholarly journals Approaches to the Cephalotaxine Skeleton Using an Intramolecular Heck Reaction.

1998 ◽  
Vol 46 (7) ◽  
pp. 1084-1089 ◽  
Author(s):  
Masazumi IKEDA ◽  
Ken-ichi HIROSE ◽  
Serry A.A. EL BIALY ◽  
Tatsunori SATO ◽  
Takayuki YAKURA ◽  
...  
Keyword(s):  
Heck Reaction ◽  
Intramolecular Heck Reaction

First total synthesis of antihypertensive natural products S-(+)-XJP and R-(−)-XJP

2014 ◽  
Vol 12 (37) ◽  
pp. 7338-7344 ◽  
Author(s):  
Chaolei Wang ◽  
Guoxiang Wei ◽  
Xue Yang ◽  
Hequan Yao ◽  
Jieyun Jiang ◽  
...  
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Heck Reaction ◽  
Intramolecular Heck Reaction

The first total synthesis of S-(+)-XJP and R-(−)-XJP has been achieved via intramolecular Heck reaction. A latent functionality strategy was implemented to circumvent the racemization in this endeavor.

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