Tetrahedron letters

The stereochemically controlled synthesis of spirocyclic ethers and lactones with medium-sized (7-, 8-, and 12-membered) carbocyclic rings by phenylthio migration: 1 …

…, KP Jenkins, M Simons, S Warren, IC Richards

Index: Chibale, Kelly; Hartley, Richard C.; Jenkins, Kevin P.; Simons, Matthew; Warren, Stuart; Richards, Ian C. Tetrahedron Letters, 1993 , vol. 34, # 42 p. 6783 - 6786

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Citation Number: 8

Abstract

Abstract 3-Methyl-4-phenylthio-1-oxaspiro [4.6] undecanes,[4.7] dodecanes,[4.11] hexadecanes and the corresponding 2-ones (lactones) can be made from cyclohepta-, octa- , and dodecanone by chain extension to the 2-phenylthio-carbaldehyde, stereoselective aldol reaction and stereospecific phenylthio migration with control over the relative (3, 4-syn or anti) and absolute (R or S at positions 3 and 4) stereochemistry.