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Synlett 1997; 1997(12): 1469-1471
DOI: 10.1055/s-1997-1066
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Synthesis of a Phenolic Analog of Aphidicolin. Diminished Stereoselection in Intramolecular 6-Exo Heck Reactions of Substrates Having a Hydrocarbon Tether

Matthew M. Abelman, Noriyuki Kado, Larry E. Overman* , Achintya K. Sarkar
  • *Department of Chemistry, 516 Physical Sciences 1, University of California, Irvine, CA 92697-2025, USA, Fax: 714-824-3866; Internet: leoverma@uci.edu
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Publication Date:
31 December 2000 (online)

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Spirotetracycle 14, generated by intramolecular Heck cyclization of 13, was converted to the phenolic analog 20 of aphidicolin. That the nature of the tether connecting insertion partners can dramatically alter diastereoselection in intramolecular Heck reactions is also demonstrated.

Heck reaction - stereocontrol - diterpene

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