(+)-Pleuromutilin synthetic studies. Direct degradation to and independent preparation of an advanced diketone intermediate. Demonstration that reconstruction of the eight-membered ring suffers from serious kinetic retardation

1988 ◽  
Vol 53 (7) ◽  
pp. 1450-1460 ◽  
Author(s):  
Leo A. Paquette ◽  
Philip C. Bulman-Page ◽  
Paul D. Pansegrau ◽  
Paul E. Wiedeman
Keyword(s):  
Membered Ring ◽  
Synthetic Studies

Synthetic studies of taxane carbon framework. A highly efficient eight-membered ring cyclization with complete stereocontrol

Tetrahedron ◽  
1992 ◽  
Vol 48 (34) ◽  
pp. 6975-6984 ◽  
Author(s):  
Takashi Furukawa ◽  
Koichiro Morihira ◽  
Yoshiaki Horiguchi ◽  
Isao Kuwajima
Keyword(s):  
Membered Ring ◽  
Highly Efficient ◽  
Carbon Framework ◽  
Synthetic Studies

Synthetic Studies of Haliclonin A: Construction of the 3-Azabicyclo[3.3.1]nonane Skeleton with a Bridge that Forms the 17-Membered Ring

Synlett ◽  
2018 ◽  
Vol 29 (06) ◽  
pp. 769-772 ◽  
Author(s):  
Satoshi Yokoshima ◽  
Tohru Fukuyama ◽  
Kensuke Orihara ◽  
Fumiki Kawagishi
Keyword(s):  
Conjugate Addition ◽  
Membered Ring ◽  
Core Structure ◽  
Ring Closing Metathesis ◽  
Macrocyclic Ring ◽  
The Core ◽  
Hydride Shift ◽  
Synthetic Studies

The core structure of haliclonin A, a 3-azabicyclo[3.3.1]­nonane with a bridge that forms a 17-membered ring, was constructed. The synthesis features a ring-closing metathesis that constructs the macrocyclic ring, the stereoselective introduction of carbon units via the intra­molecular cyclopropanation of a diazoester, the conjugate addition of an organocopper reagent, and the formation of 3-azabi­cyclo­[3.3.1]­nonane skeleton via an unexpected 1,5-hydride shift.

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