Controlling benzylic functionality and stereochemistry: 1. Synthesis of the secopseudopterosin aglycone

Journal Article (Journal Article)

Directed, homogeneous hydrogenation of 1-(1-hydroxymethylethyl)-5-methoxy-3,4-dihydronaphthalene (7), followed by protection and selective benzylic oxidation gave the 1-oxo-(4R*, 11R*) compound (13). After addition of MeCeCl2, the natural C-1 stereochemistry was established by intramolecular hydride delivery from the di-t-butylsilylether. Final elaboration of the sidechain and the Ar ring substituents gave the secopseudopterosin aglycone other (3). © 1991.

Full Text

Duke Authors

Cited Authors

  • McCombie, SW; Cox, B; Lin, SI; Ganguly, AK; McPhail, AT

Published Date

  • May 6, 1991

Published In

Volume / Issue

  • 32 / 19

Start / End Page

  • 2083 - 2086

International Standard Serial Number (ISSN)

  • 0040-4039

Digital Object Identifier (DOI)

  • 10.1016/S0040-4039(00)71242-1

Citation Source

  • Scopus