Download PDF
Synfacts 2022; 18(02): 0123
DOI: 10.1055/s-0041-1737239
Synthesis of Natural Products and Potential Drugs

Synthesis of Corannulene

Contributor(s):
Erick M. Carreira
,
Viktoria C. Gerken
Scott LT, Hashemi MM, Meyer DT, Warren HB. University of Nevada, Reno, USA
Corannulene. A Convenient New Synthesis.

J. Am. Chem. Soc. 1991;
113: 7082-7084
DOI: 10.1021/ja00018a082.
CrossrefGoogle Scholar
› Further Information
 
 PDF Download Permissions and Reprints

Key words

corannulene - hydrocarbon synthesis - Corey–Fuchs reaction - flash vacuum pyrolysis - vinylidene C–H insertion

Significance

Corannulene is a polycyclic aromatic hydrocarbon consisting of a cyclopentane ring that is fused with five benzene rings. The bowl-shaped molecule was first synthesized by Bath and Lawton in 1966 (J. Am. Chem. Soc. 1966, 88, 380). In 1991, Scott and co-workers presented a simplified synthesis featuring flash vacuum pyrolysis to access the product.


#

Comment

Knoevenagel condensation and Diels–Alder cycloaddition give access to tetracyclic diester F. The corresponding aldehyde G is then converted in a Corey–Fuchs reaction to dialkyne I. Flash vacuum pyrolysis putatively furnishes vinylidene J which is trapped to yield corannulene. Interestingly, gem-dibromoalkene H also yields corannulene under flash vacuum pyrolysis conditions by loss of bromine atoms.


#
#

Publication History

Article published online:
18 January 2022

© 2022. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany


   Permissions and Reprints