Total Synthesis of Scytophycin C. 2. Coupling Reaction of the C(1)−C(18) Segment and the C(19)−C(31) Segment, a Key Macrolactonization, and the Crucial Terminal Amidation Reaction

2003 ◽  
Vol 5 (20) ◽  
pp. 3583-3586 ◽  
Author(s):  
Ryoichi Nakamura ◽  
Keiji Tanino ◽  
Masaaki Miyashita
Keyword(s):  
Total Synthesis ◽  
Coupling Reaction ◽  
Amidation Reaction ◽  
Scytophycin C

scholarly journals Stereocontrolled total synthesis of (+)-vinblastine

2003 ◽  
Vol 75 (1) ◽  
pp. 29-38 ◽  
Author(s):  
Satoshi Yokoshima ◽  
T. Ueda ◽  
S. Kobayashi ◽  
A. Sato ◽  
Takeshi Kuboyama ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Coupling Reaction ◽  
Radical Cyclization ◽  
Critical Coupling ◽  
Efficient Manner ◽  
Complete Control ◽  
Highly Efficient ◽  
Indole Synthesis

Stereocontrolled total synthesis of (+)-vinblastine (1) has been achieved using a novel radical-mediated indole synthesis developed in our laboratories. The isothiocyanate 18, prepared readily from quinoline 17, underwent a facile addition of the malonate anion to give 19. The o-alkenylthioanilide 19 was then converted to indole 20 by radical cyclization and protection. (−)-Vindoline (2) was prepared from this key intermediate 20 in a highly efficient manner. The indole core of the 11-membered intermediate 3 was constructed similarly from quinoline. The critical coupling reaction between 2 and the chloroindolenine derived from 3 proceeded with complete control of stereochemistry to give the desired product 66 in 97 % yield, which could be successfully converted to (+)-vinblastine (1).

Total Synthesis of (±)-Cassumunins A–C and Curcumin Analogues

Synthesis ◽  
2020 ◽  
Vol 52 (10) ◽  
pp. 1561-1575 ◽  
Author(s):  
Faiz Ahmed Khan ◽  
Mulla Althafh Hussain
Keyword(s):  
Total Synthesis ◽  
Claisen Rearrangement ◽  
Aldol Condensation ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Full Account ◽  
Curcumin Analogues ◽  
Cross Coupling Reaction ◽  
Sigmatropic Shift ◽  
Novel Approaches

A full account of the total synthesis of (±)-cassumunins A–C – superior antioxidants and anti-inflammatory agents – is given. Two novel approaches were developed for synthesizing cassumunins. The total synthesis of cassumunins A and B was accomplished in five linear steps from a known aldehyde in good overall yields of 50 and 43%, respectively, featuring a cascade [3,3]-sigmatropic shift (the Claisen rearrangement) and Heck cross-coupling reaction. Consequently, the total synthesis of cassumunin C was accomplished in three linear steps from a known alcohol with an overall yield of 53%. The key features involved in this synthesis are tandem [3,3]-sigmatropic shift, SN2′ reaction, and aldol condensation. Moreover, a total of eighteen symmetrical and unsymmetrical curcumin analogues were synthesized.

ChemInform Abstract: Total Synthesis of (-)-Macrocarpal C. Stereoselective Coupling Reaction with a Novel Hexasubstituted Benzene Cr(CO)3 Complex as a Biomimetic Chiral Benzyl Cation Equivalent.

ChemInform ◽  
2010 ◽  
Vol 30 (22) ◽  
pp. no-no
Author(s):  
Tetsuaki Tanaka ◽  
Hidenori Mikamiyama ◽  
Kimiya Maeda ◽  
Chuzo Iwata ◽  
Yasuko In ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Coupling Reaction ◽  
Benzyl Cation

Total synthesis of actinobolin from d-glucose by way of the stereoselective three-component coupling reaction

Tetrahedron ◽  
2006 ◽  
Vol 62 (29) ◽  
pp. 6926-6944 ◽  
Author(s):  
Satoshi Imuta ◽  
Hiroki Tanimoto ◽  
Miho K. Momose ◽  
Noritaka Chida
Keyword(s):  
Total Synthesis ◽  
Coupling Reaction ◽  
Three Component Coupling
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