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Synthesis 1995; 1995(6): 630-632
DOI: 10.1055/s-1995-3987
short paper
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A Simple Approach to the Synthesis of the Chiral Substituted Chroman Ring of Calophyllum Coumarins

Prashant P. Deshpande, David C. Baker*
  • *Department of Chemistry, The University of Tennessee, Knoxville, Tennessee 37996-1600, USA, Fax +1(615)9741536; E-mail Baker@novell.chem.utk.edu
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Publication Date:
31 December 2000 (online)

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A stereoselective synthesis of the chiral 2,3-dimethylchroman-4-ol ring of the calophyllum coumarins is described. The chiral centers at C-3 and C-4 (chroman numbering) were introduced using (Z)-crotyldiisopinocampheylborane, and the chiral center at C-2 was introduced via mercury-assisted cyclization and demercuration, giving the required trans, trans-Me-Me-OH substituted chroman (benzo[b]pyran) ring.

calanolide - inophyllum - (Z)-crotyldiisopinocampheylborane - 2,3-dimethylchroman-4-ol - Hg(OAc)2 cyclization