Studies related to the synthesis of racemic pederin: Part 1. Synthesis of ethyl pederate and benzoylselenopederic acid | Health & Environmental Research Online (HERO)

Health & Environmental Research Online (HERO)

Print Feedback Export to File

This record has one attached file:

Citation
Tags

HERO ID

5379992

Reference Type

Journal Article

Title

Studies related to the synthesis of racemic pederin: Part 1. Synthesis of ethyl pederate and benzoylselenopederic acid

Author(s)

Willson, TM; Kocienski, P; Jarowicki, K; Isaac, K; Faller, A; Campbell, SF; Bordner, J

Year

1990

Is Peer Reviewed?

Journal

Tetrahedron
ISSN: 0040-4020

Volume

Issue

Page Numbers

1757-1766

Language

English

Abstract

BIOSIS COPYRIGHT: BIOL ABS. The first in a series of 2 papers on the synthesis of the insect toxin pederin (1) begins with a discussion of syntheses of the ring A fragments (|)-ethyl pederate (2) and (|)-benzoylselenopederic acid (4). A silicon-mediated intramolecular cyclisation of a chloroformate onto an allyl silane (11) was used to introduce the ring A methylene group at C-4 in ethyl pederate. Conjugate addition of phenylselenomethyl-lithium to the alpha,beta-unsaturated lactone (19) was a key step in the construction (4).