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Synlett 1997; 1997(10): 1161-1162
DOI: 10.1055/s-1997-985
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Elaboration of S-(-)-α-Pinene into Functionalized Bicyclo[4.2.1]nonane Framework of Mediterraneols

Goverdhan Mehta* , P. V.R. Acharyulu, K. Subba Reddy, Jayant D. Umarye
  • *Molecular Design and Synthesis Laboratory of JNCASR and School of Chemistry, University of Hyderabad, Hyderabad 500 046, India
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Publication Date:
31 December 2000 (online)

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A two-carbon ring expansion of (-)-α-pinene 1 to bicyclo[5.1.1]nonane system (+)-12 and 1,2-cationic rearrangement provides an entry into a functionalized bicyclo[4.2.1]nonane derivative, representing the carbocyclic skeleton, present in the novel marine diterpenes, mediterraneols.

"push-pull" cyclopropane fragmentation - two-carbon ring expansion - bicyclo[4.2.1.]nonane - marine natural products