Studies related to the synthesis of (±)-pederin. part 1. Synthesis of ethyl pederate and benzoylselenopederic acid

Add time:07/17/2019    Source:sciencedirect.com

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 α,β-unsaturated lactone (19) was a key step in the construction of (4).

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