Heterocyclic Compounds
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ChemInform Abstract: Enantioselective Total Synthesis of (-)-Monic Acid C via Carbosulfenylation of a Dihydropyran.
First published: May 30, 1989
Abstract
The dihydropyran (I) reacts with (-)-1-borneol (II) and bromine to give the bromo ethers (III) and (IV).
ChemInform Abstract
The dihydropyran (I) reacts with (-)-1-borneol (II) and bromine to give the bromo ethers (III) and (IV). These are converted into the dihydrofuropyranone (X) which undergoes carbosulfenylation, directly followed by cleavage and elimination, forming the oxopropyldihydropyranylacetic acids (XIV). The stereoisomer (XIVa) is transformed into monic acid C (XVI) via the aldehyde (XV).
