Second Approach to the Construction of a Pentacyclic Ring System for Neosurugatoxin

Kunisuke OKADA; Yasushi MIZUNO; Hideo TANINO; Hisae KAKOI; Shoji INOUE

doi:10.1248/cpb.40.1110

Kunisuke OKADA, Yasushi MIZUNO, Hideo TANINO, Hisae KAKOI, Shoji INOUE

Author information

Keywords: spiro-6-bromo-2-oxoindoline dervative, (E)-6-bromo-3-ethoxycarbonylmethylene-2-oxoindoline, Diels-Alder adduct, trans-1, 3-pentadiene, neosurugatoxin, marine toxin, neosurugatoxin formal synthesis, 2-(methylthio)ethyl 6'-bromo-1', 2'-dihydro-6-methyl-2'-oxospiro[4-cyclohexene1, 3'-[3H]indole]-2-carboxylate

JOURNAL FREE ACCESS

1992 Volume 40 Issue 5 Pages 1110-1115

DOI https://doi.org/10.1248/cpb.40.1110

Details

Abstract

The Diels-Alder adduct obtained from (E)-6-bromo-3-ethoxycarbonylmethylene-2-oxoindoline and trans-1, 3-pentadiene was successfully transformed into the diacetate of the aglycone of neosurugatoxin, which is the key intermediate in our first total synthesis of neosurugatoxin in 16 steps.

Corresponding author

Register with J-STAGE for free!